Benzyloxypyrimidine derivative, agricultural/ horticultural insecticide comprising derivative and method for using same

ABSTRACT

A benzyloxypyrimidine derivative represented by the formula (I) 
                         
wherein R 1  is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, an alkoxyalkyl group and the like; R 2  and R 3  are each a hydrogen atom, an alkyl group and the like; X is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, a trialkylsilyl group and the like; A is a oxygen atom and the like, and m is an integer of 0-5, or a salt thereof, and an agrohorticultural insecticide containing the compound as an active ingredient and a method of use thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This patent application is the U.S. national phase of InternationalPatent Application No. PCT/JP2011/079847, filed Dec. 22, 2011, whichclaims the benefit of Japanese Patent Application No. 2010-287777, filedon Dec. 24, 2010, and Japanese Patent Application No. 2011-181052, filedAug. 23, 2011, which are incorporated by reference in their entiretiesherein.

TECHNICAL FIELD

The present invention relates to an agrohorticultural insecticidecontaining a novel pyrimidine derivative or a salt thereof as an activeingredient, and a method of use thereof.

BACKGROUND ART

While the pyrimidine derivative described in patent document 1 isdisclosed to be useful as an insecticide, it has a different structurefrom the pyrimidine derivative of the present invention. While thepyrimidine derivative described in patent document 2 is disclosed to beuseful as an insecticide, a compound having a substituent disclosed inthe present invention at the 4-position of pyrimidine is not disclosed.

-   patent document 1: WO 2010/064688-   patent document 2: WO 1993/006091

SUMMARY OF THE INVENTION Problems to be Solved by the Invention

In crop manufacturing in agricultural and horticultural fields, damagescaused by insect pests are still serious, and development of novelagrohorticultural insecticides and acaricides is desired due togeneration of insect pests resistant to known agents, and the like.Since various labor saving farm works are required due to increasingnumbers of the aged farm working population, creation ofagrohorticultural insecticides having suitable properties for the farmworks is also demanded.

Means of Solving the Problems

The present inventors have conducted intensive studies in an attempt todevelop a novel agrohorticultural insecticide, and have found that thebenzyloxypyrimidine derivative represented by the formula (I) of thepresent invention is a novel compound not described in literatures, anduseful as an agrohorticultural insecticide, which resulted in thecompletion of the present invention.

Accordingly, the present invention relates to

-   [1] a benzyloxypyrimidine derivative represented by the formula (I):

wherein, R¹ is

-   (a1) a hydrogen atom;-   (a2) a (C₁-C₆)alkyl group;-   (a3) a (C₃-C₇)cycloalkyl group (said cycloalkyl group is optionally    fused with a benzene ring);-   (a4) a (C₂-C₆)alkenyl group;-   (a5) a (C₂-C₆)alkynyl group;-   (a6) a halo(C₁-C₆)alkyl group;-   (a7) a halo(C₃-C₆)cycloalkyl group;-   (a8) a halo(C₂-C₆)alkenyl group;-   (a9) a halo(C₂-C₆)alkynyl group;-   (a10) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (a11) a (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (a12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group;-   (a13) a (C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group;-   (a14) a (C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group;-   (a15) a halo(C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (a16) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (a17) a halo(C₁-C₆)alkylthio(C₁-C₆)alkyl group;-   (a18) a halo(C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group;-   (a19) a halo(C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group;-   (a20) a (C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group;-   (a21) a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group;-   (a22) an aryl(C₁-C₆)alkyl group;-   (a23) an aryl(C₁-C₆)alkyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₃-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ may be the same or different and each is a    hydrogen atom, a (C₁-C₆)alkyl group, a (C₃-C₆)cycloalkyl group, a    (C₂-C₆)alkenyl group, a (C₂-C₆)alkynyl group, a    (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a    halo(C₃-C₆)cycloalkyl group, a halo(C₂-C₆)alkenyl group, a    halo(C₂-C₆)alkynyl group, a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group,    a phenyl group, or a phenyl(C₁-C₆)alkyl group;-   (a24) a cyano(C₁-C₆)alkyl group;-   (a25) a nitro (C₁-C₆)alkyl group;-   (a26) a R⁴(R⁵)N(C₁-C₆)alkyl group wherein R⁴ and R⁵ are as defined    above;-   (a27) a (R⁴)OC(C₁-C₆)alkyl group wherein R⁴ is as defined above;-   (a28) a (R⁴)O₂C(C₁-C₆)alkyl group wherein R⁴ is as defined above;-   (a29) a R⁴(R⁵)NCO(C₁-C₆)alkyl group wherein R⁴ and R⁵ are as defined    above;-   (a30) an aryl group;-   (a31) an aryl group having, on the ring, the same or different 1 to    5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkyl    group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h)    a halo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (j) a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio    group, (l) a (C₁-C₆)alkylsulfinyl group, (m) a    halo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl    group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a    (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) a phenoxy group;-   (a32) an arylsulfonyl group;-   (a33) an arylsulfonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a34) an arylcarbonyl group;-   (a35) an arylcarbonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a36) an arylthio(C₁-C₆)alkyl group;-   (a37) an arylthio(C₁-C₆)alkyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (l) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a38) an arylsulfinyl(C₁-C₆)alkyl group;-   (a39) an arylsulfinyl(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a40) an arylsulfonyl(C₁-C₆)alkyl group;-   (a41) an arylsulfonyl(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a42) an arylcarbonyloxy(C₁-C₆)alkyl group;-   (a43) an arylcarbonyloxy(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a44) a (C₁-C₆)alkylcarbonyl group;-   (a45) a (C₁-C₆)alkoxycarbonyl group;-   (a47) a R⁴(R⁵)N carbonyloxy(C₁-C₆)alkyl group wherein R⁴ and R⁵ are    as defined above;-   (a48) a tri(C₁-C₆)alkylsilyl group wherein the alkyl groups may be    the same or different;-   (a49) a (C₁-C₆)alkoxy(C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (a50) a (C₁-C₆)alkoxycarbonyloxy(C₁-C₆)alkyl group;-   (a51) a (C₁-C₆)alkyl(C₁-C₆)sulfonyl group;-   (a52) a heterocyclic group;-   (a53) a heterocyclic group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) an oxo group;-   (a54) a heterocyclyl(C₁-C₆)alkyl group;-   (a55) a heterocyclyl(C₁-C₆)alkyl group having, on the ring, the same    or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) an oxo group;-   (a56) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl    groups of the tri(C₁-C₆)alkylsilyl may be the same or different; or-   (a57) a R⁴(R⁵)NCO group wherein R⁴ and R⁵ are as defined above,-   A is —O—, —S—, —SO— or —SO₂—.-   R² and R³ may be the same or different, and each is-   (b1) a hydrogen atom;-   (b2) a (C₁-C₆)alkyl group;-   (b3) a (C₃-C₆)cycloalkyl group;-   (b4) a (C₂-C₆)alkenyl group;-   (b5) a (C₂-C₆)alkynyl group;-   (b6) a halo(C₁-C₆)alkyl group;-   (b7) a halo(C₃-C₆)cycloalkyl group;-   (b8) a halo(C₂-C₆)alkenyl group;-   (b9) a halo(C₂-C₆)alkynyl group;-   (b10) a (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (b11) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (b12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; or-   (b13) a (C₁-C₆)alkoxycarbonyl group,    X may be the same or different, and each is-   (c1) a hydrogen atom;-   (c2) a halogen atom;-   (c3) a hydroxyl group;-   (c4) a cyano group;-   (c5) a nitro group;-   (c6) a N(R⁴)(R⁵) group wherein R⁴ and R⁵ are as defined above;-   (c7) a N(R⁴)CO(R⁵) group wherein R⁴ and R⁵ are as defined above;-   (c8) a N(R⁴) SO₂(R⁵) group wherein R⁴ and R⁵ are as defined above;-   (c9) a N(R⁴)CO₂(R⁵) group wherein R⁴ and R⁵ are as defined above;-   (c10) a CO(R⁴) group wherein R⁴ is as defined above;-   (c11) a CO₂(R⁴) group wherein R⁴ is as defined above;-   (c12) a CON(R⁴)(R⁵) group wherein R⁴ and R⁵ are as defined above;-   (c13) a C(R⁴)═NOR⁵ group wherein R⁴ and R⁵ are as defined above;-   (c14) a (C₁-C₁₂)alkyl group;-   (c15) a (C₂-C₁₂)alkenyl group;-   (c16) a (C₂-C₁₂)alkynyl group;-   (c17) a (C₃-C₃₂)cycloalkyl group;-   (c18) a halo(C₁-C₁₂)alkyl group;-   (c19) a halo(C₂-C₁₂)alkenyl group;-   (c20) a halo(C₂-C₁₂)alkynyl group;-   (c21) a halo(C₃-C₁₂)cycloalkyl group;-   (c22) a tri(C₁-C₁₂)alkylsilyl group wherein the alkyl groups may be    the same or different;-   (c23) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl    groups of the tri(C₁-C₆)alkylsilyl may be the same or different;-   (c24) a (C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkyl group;-   (c25) a halo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkyl group;-   (c26) a (C₃-C₁₂)cycloalkyl(C₃-C₁₂)cycloalkyl group;-   (c27) a (C₁-C₁₂)alkoxy group;-   (c28) a (C₂-C₁₂)alkenyloxy group;-   (c29) a (C₂-C₁₂)alkynyloxy group;-   (c30) a (C₃-C₁₂)cycloalkyloxy group (said cycloalkyl is optionally    fused with a benzene ring);-   (c31) a halo(C₁-C₁₂)alkoxy group;-   (c32) a halo(C₂-C₁₂)alkenyloxy group;-   (c33) a halo(C₂-C₁₂)alkynyloxy group;-   (c34) a halo(C₃-C₁₂)cycloalkyloxy group (said cycloalkyl is    optionally fused with a benzene ring);-   (c35) a (C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkoxy group;-   (c36) a halo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkoxy group;-   (c37) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (c38) a halo(C₁-C₆)alkoxy(C₁-C₆)alkoxy group;-   (c39) a (C₁-C₆)alkoxyhalo(C₁-C₆)alkoxy group;-   (c40) a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkoxy group;-   (c41) a mercapto group;-   (c42) a (C₁-C₁₂)alkylthio group;-   (c43) a (C₂-C₁₂)alkenylthio group;-   (c44) a (C₂-C₁₂)alkynylthio group;-   (c45) a (C₃-C₁₂)cycloalkylthio group;-   (c46) a halo(C₁-C₁₂)alkylthio group;-   (c47) a halo(C₂-C₁₂)alkenylthio group;-   (c48) a halo(C₂-C₁₂)alkynylthio group;-   (c49) a halo(C₃-C₁₂)cycloalkylthio group;-   (c50) a (C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylthio group;-   (c51) a halo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylthio group;-   (c52) a (C₁-C₆)alkoxy(C₁-C₆)alkylthio group;-   (c53) a halo(C₁-C₆)alkoxy(C₁-C₆)alkylthio group;-   (c54) a (C₁-C₆)alkoxyhalo(C₁-C₆)alkylthio group;-   (c55) a halo(C₁-C₆)alkoxyhalo(C₁-C₆)alkylthio group;-   (c56) a (C₁-C₁₂)alkylsulfinyl group;-   (c57) a (C₂-C₁₂)alkenylsulfinyl group;-   (c58) a (C₂-C₁₂)alkynylsulfinyl group;-   (c59) a (C₃-C₁₂)cycloalkylsulfinyl group;-   (c60) a halo(C₁-C₁₂)alkylsulfinyl group;-   (c61) a halo(C₂-C₁₂)alkenylsulfinyl group;-   (c62) a halo(C₂-C₁₂)alkynylsulfinyl group;-   (c63) a halo(C₃-C₁₂)cycloalkylsulfinyl group;-   (c64) a (C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfinyl group;-   (c65) a halo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfinyl group;-   (c66) a (C₁-C₁₂)alkylsulfonyl group;-   (c67) a (C₂-C₁₂)alkenylsulfonyl group;-   (c68) a (C₂-C₁₂)alkynylsulfonyl group;-   (c69) a (C₃-C₁₂)cycloalkylsulfonyl group;-   (c70) a halo(C₁-C₁₂)alkylsulfonyl group;-   (c71) a halo(C₂-C₁₂)alkenylsulfonyl group;-   (c72) a halo(C₂-C₁₂)alkynylsulfonyl group;-   (c73) a halo(C₃-C₁₂)cycloalkylsulfonyl group;-   (c74) a (C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfonyl group;-   (c75) a halo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfonyl group;-   (c76) an aryl group;-   (c77) an aryl group having, on the ring, the same or different 1 to    5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c78) an aryl(C₁-C₆)alkyl group;-   (c79) an aryl(C₁-C₆)alkyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c80) an aryloxy group;-   (c81) an aryloxy group having, on the ring, the same or different 1    to 5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c82) an aryloxy(C₁-C₆)alkyl group;-   (c83) an aryloxy(C₁-C₆)alkyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c84) an arylthio group;-   (c85) an arylthio group having, on the ring, the same or different 1    to 5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₂-C₆)alkylsulfinyl group, (s) a halo(C₂-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c86) a halo(C₁-C₆)alkylenedioxy group;-   (c87) a (C₁-C₆)alkoxy(C₁-C₆)alkoxy group;-   (c88) a (C₃-C₈)alkylene group;-   (c89) a (C₁-C₆)alkyl(C₃-C₈)alkylene group;-   (c90) a tri(C₁-C₁₂)alkylsilyloxy group wherein the alkyl groups may    be the same or different;-   (c91) a tri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkoxy group wherein the alkyl    groups may be the same or different;-   (c92) a di(C₁-C₁₂)alkylhalo(C₁-C₆)alkylsilyl group wherein the alkyl    groups may be the same or different;-   (c93) a di(C₁-C₁₂)alkyl(C₁-C₆)alkylthio(C₁-C₆)alkylsilyl group    wherein the alkyl groups may be the same or different;-   (c94) a di(C₁-C₁₂)alkylhydroxysilyl group wherein the alkyl groups    may be the same or different;-   (c95) a di(C₁-C₁₂)alkylhydrosilyl group wherein the alkyl groups may    be the same or different;-   (c96) a di(C₁-C₁₂)alkylphenylsilyl group wherein the alkyl groups    may be the same or different;-   (c97) a (C₁-C₆)alkylthio(C₁-C₆)alkoxy group;-   (c98) a (C₁-C₆)alkylsulfinyl(C₁-C₆)alkoxy group;-   (c99) a (C₁-C₆)alkylsulfonyl(C₁-C₆)alkoxy group;-   (c100) a (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy group;-   (c101) a (C₁-C₆)alkylcarbonyl(C₁-C₆)alkoxy group;-   (c102) a cyano(C₁-C₆)alkoxy group;-   (c103) an aryl(C₁-C₆)alkoxy group wherein the alkoxy moiety may be    halogenated;-   (c104) an aryl(C₁-C₆)alkoxy group wherein the alkoxy moiety may be    halogenated, which has, on the ring, the same or different 1 to 5    substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₂-C₆)alkylsulfinyl group, (s) a halo(C₂-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c105) a hydroxy(C₁-C₆)alkyl group;-   (c106) a (C₁-C₆)alkylthio(C₁-C₆)alkylcarbonyl group;-   (c107) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group;-   (c108) a tri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkylthio group wherein the    alkyl groups of the tri(C₁-C₁₂)alkylsilyl may be the same or    different;-   (c109) a tri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkylsulfinyl group wherein the    alkyl groups of the tri(C₁-C₁₂)alkylsilyl may be the same or    different;-   (c110) a tri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkylsulfonyl group wherein the    alkyl groups of the tri(C₁-C₁₂)alkylsilyl may be the same or    different;-   (c111) a R⁴(R⁵)N(C₁-C₆)alkyl group wherein R⁴ and R⁵ are as defined    above;-   (c112) a heterocyclic group;-   (c113) a heterocyclic group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c114) a heterocyclyloxy group;-   (c115) a heterocyclyloxy group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c116) a heterocyclylthio group;-   (c117) a heterocyclylthio group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c118) a heterocyclylsulfinyl group;-   (c119) a heterocyclylsulfinyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c120) a heterocyclylsulfonyl group;-   (c121) a heterocyclylsulfonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c122) a heterocyclyl(C₁-C₆)alkyloxy group;-   (c123) a heterocyclylalkyloxy group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c124) a (C₁-C₁₂)alkyl(C₃-C₁₂)cycloalkyl group;-   (c125) a halo(C₁-C₁₂)alkyl(C₃-C₁₂)cycloalkyl group;-   (c126) a (C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group;-   (c127) a di(C₁-C₁₂)alkylbenzylsilyl group wherein the alkyl groups    may be the same or different;-   (c128) a heterocyclyl(C₁-C₆)alkyl group;-   (c129) a heterocyclyl(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group,-   (c130) a heterocyclyloxy(C₁-C₆)alkyl group; or-   (c131) a heterocyclyloxy(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group, or-   X can form, together with the adjacent R² or R³, (C132) a bicyclo    ring, wherein the bicyclo ring optionally has the same or different    one or more substituents selected from (a) a halogen atom, (b) a    (C₁-C₆)alkyl group, (c) a halo(C₁-C₆)alkyl group, (d) a    (C₁-C₆)alkoxy group, (e) a halo(C₁-C₆)alkoxy group, (f) a    (C₁-C₆)alkylthio group, (g) a halo(C₁-C₆)alkylthio group, (h) a    (C₁-C₆)alkylsulfinyl group, (i) a halo(C₁-C₆)alkylsulfinyl    group, (j) a (C₁-C₆)alkylsulfonyl group, and (k) a    halo(C₁-C₆)alkylsulfonyl group; or,-   X can form, together with the adjacent X on an aromatic ring,-   (C133) a bicyclo ring or (C134) a fused ring, wherein the bicyclo    ring or fused ring optionally has the same or different one or more    substituents selected from (a) a halogen atom, (b) a (C₁-C₆)alkyl    group, (c) a halo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxy group, (e)    a halo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g) a    halo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) a    halo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group,    and (k) a halo(C₁-C₆)alkylsulfonyl group, and-   m is an integer of 0 to 5,    or salts thereof;-   [2] the benzyloxypyrimidine derivative of the above-mentioned [1],    wherein m is as defined in the above-mentioned [1], R¹ is-   (a1) a hydrogen atom;-   (a2) a (C₁-C₆)alkyl group;-   (a3) a (C₃-C₇)cycloalkyl group (said cycloalkyl group is optionally    fused with a benzene ring);-   (a4) a (C₂-C₆)alkenyl group;-   (a5) a (C₂-C₆)alkynyl group;-   (a6) a halo(C₁-C₆)alkyl group;-   (a8) a halo(C₂-C₆)alkenyl group;-   (a10) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (a11) a (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (a12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group;-   (a13) a (C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group;-   (a14) a (C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group;-   (a16) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (a22) an aryl(C₁-C₆)alkyl group;-   (a23) an aryl(C₁-C₆)alkyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group,    (p)_(a) (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined in the above-mentioned [1];-   (a24) a cyano(C₁-C₆)alkyl group;-   (a30) an aryl group;-   (a31) an aryl group having, on the ring, the same or different 1 to    5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkyl    group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h)    a halo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (j) a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio    group, (l) a (C₁-C₆)alkylsulfinyl group, (m) a    halo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl    group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a    (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) a phenoxy group;-   (a32) an arylsulfonyl group;-   (a33) an arylsulfonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a34) an arylcarbonyl group;-   (a35) an arylcarbonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a44) a (C₁-C₆)alkylcarbonyl group;-   (a52) a heterocyclic group;-   (a53) a heterocyclic group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) an oxo group;-   (a54) a heterocyclyl(C₁-C₆)alkyl group;-   (a55) a heterocyclyl(C₁-C₆)alkyl group having, on the ring, the same    or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) an oxo group;-   (a56) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl    groups of the tri(C₁-C₆)alkylsilyl may be the same or different; or-   (a57) a R⁴(R⁵)NCO group wherein R⁴ and R⁵ are as defined above,    A is —O—, —S—, —SO— or —SO₂—,    R² and R³ may be the same or different and each is-   (b1) a hydrogen atom;-   (b2) a (C₁-C₆)alkyl group;-   (b3) a (C₃-C₆)cycloalkyl group;-   (b6) a halo(C₁-C₆)alkyl group;-   (b11) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (b12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; or-   (b13) a (C₁-C₆)alkoxycarbonyl group, and    X may be the same or different and each is-   (c1) a hydrogen atom;-   (c2) a halogen atom;-   (c5) a nitro group;-   (c14) a (C₁-C₁₂)alkyl group;-   (c17) a (C₃-C₁₂)cycloalkyl group;-   (c18) a halo(C₁-C₁₂)alkyl group;-   (c21) a halo(C₃-C₁₂)cycloalkyl group;-   (c22) a tri(C₁-C₁₂)alkylsilyl group wherein the alkyl groups may be    the same or different;-   (c27) a (C₁-C₁₂)alkoxy group;-   (c30) a (C₃-C₁₂)cycloalkyloxy group (said cycloalkyl is optionally    fused with a benzene ring);-   (c31) a halo(C₁-C₁₂)alkoxy group;-   (c38) a halo(C₁-C₆)alkoxy(C₁-C₆)alkoxy group;-   (c42) a (C₁-C₁₂)alkylthio group;-   (c46) a halo(C₁-C₁₂)alkylthio group;-   (c56) a (C₁-C₁₂)alkylsulfinyl group;-   (c66) a (C₁-C₁₂)alkylsulfonyl group;-   (c80) an aryloxy group;-   (c81) an aryloxy group having, on the ring, the same or different 1    to 5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c112) a heterocyclic group;-   (c113) a heterocyclic group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c114) a heterocyclyloxy group;-   (c115) a heterocyclyloxy group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c130) a heterocyclyloxy(C₁-C₆)alkyl group; or-   (c131) a heterocyclyloxy(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group, or-   X can form, together with the adjacent R² or R³, (C132) a bicyclo    ring, wherein the bicyclo ring optionally has the same or different    one or more substituents selected from (a) a halogen atom, (b) a    (C₁-C₆)alkyl group, (c) a halo(C₁-C₆)alkyl group, (d) a    (C₁-C₆)alkoxy group, (e) a halo(C₁-C₆)alkoxy group, (f) a    (C₁-C₆)alkylthio group, (g) a halo(C₁-C₆)alkylthio group, (h) a    (C₁-C₆)alkylsulfinyl group, (i) a halo(C₁-C₆)alkylsulfinyl    group, (j) a (C₁-C₆)alkylsulfonyl group, and (k) a    halo(C₁-C₆)alkylsulfonyl group; or,-   X can form, together with the adjacent X on an aromatic ring, (C133)    a bicyclo ring or (C134) a fused ring, wherein the bicyclo ring or    fused ring optionally has the same or different one or more    substituents selected from (a) a halogen atom, (b) a (C₁-C₆)alkyl    group, (c) a halo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxy group, (e)    a halo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g) a    halo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) a    halo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group,    and (k) a halo(C₁-C₆)alkylsulfonyl group,    or salts thereof;-   [3] an agrohorticultural insecticide comprising the    benzyloxypyrimidine derivative according to the above-mentioned [1]    or [2] or a salt thereof as an active ingredient;-   [4] a method of using an agrohorticultural insecticide, which    comprises treating a plant or soil with the active ingredient of the    agrohorticultural insecticide according to the above-mentioned [3];-   [5] use of the benzyloxypyrimidine derivative according to the    above-mentioned [1] or [2] or a salt thereof as an agrohorticultural    insecticide;-   [6] a method of controlling an agrohorticultural pest, which    comprises treating a plant or soil with an effective amount of the    benzyloxypyrimidine derivative according to the above-mentioned [1]    or [2] or a salt thereof;-   [7] an ectoparasite controlling agent comprising the    benzyloxypyrimidine derivative according to the above-mentioned [1]    or [2] or a salt thereof as an active ingredient;-   [8] a method of controlling an ectoparasite, which comprises    treating the ectoparasite with an effective amount of the    benzyloxypyrimidine derivative according to the above-mentioned [1]    or [2] or a salt thereof;    and the like.

Effect of the Invention

The benzyloxypyrimidine derivative of the present invention or a saltthereof has a superior effect as an agrohorticultural insecticide. Onthe other hand, the derivative shows an effect on pests being parasiticin pet animals such as dogs and cats, and domestic animals such ascattle, sheep and the like.

DESCRIPTION OF EMBODIMENTS

In the definition of the benzyloxypyrimidine derivative of the presentinvention represented by the formula (I), the “halo” means a “halogenatom”, and is a chlorine atom, a bromine atom, an iodine atom or afluorine atom. The “(C₁-C₆)alkyl group” is a straight chain or branchedchain alkyl group having a carbon number of 1 to 6, for example, amethyl group, an ethyl group, a normal propyl group, an isopropyl group,a normal butyl group, an isobutyl group, a secondary butyl group, atertiary butyl group, a normal pentyl group, an isopentyl group, atertiary pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, a1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, anormal hexyl group, an isohexyl group, a 1,1,2-trimethylpropyl group andthe like. The “(C₂-C₆)alkenyl group” is a straight chain or branchedchain alkenyl group having a carbon number of 2 to 6, for example, avinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenylgroup, a 1,1-dimethyl-2-propenyl group, a 2-methyl-1-propenyl group, apentenyl group, a 1-hexenyl group and the like. The “(C₂-C₆)alkynylgroup” is a straight chain or branched chain alkynyl group having acarbon number of 2 to 6, for example, an ethynyl group, a 1-propynylgroup, a 2-propynyl group, a 1-methyl-2-propynyl group, a1,1-dimethyl-2-propynyl group, a 1-butynyl group, a 2-butynyl group, a3-butynyl group, a 3-methyl-1-propynyl group, a 2-methyl-3-propynylgroup, a pentynyl group, a 1-hexynyl group and the like.

The “(C₁-C₁₂)alkyl group” is a straight chain or branched chain alkylgroup having a carbon number of 1 to 12, for example, a methyl group, anethyl group, a normal propyl group, an isopropyl group, a normal butylgroup, an isobutyl group, a secondary butyl group, a tertiary butylgroup, a normal pentyl group, an isopentyl group, a tertiary pentylgroup, a neopentyl group, a 2,3-dimethylpropyl group, a 1-ethylpropylgroup, a 1-methylbutyl group, a normal hexyl group, an isohexyl group, a1,1,2-trimethylpropyl group, a heptyl group, an octyl group, a nonylgroup, a decyl group, an undecyl group, a dodecyl group and the like.The “(C₂-C₁₂)alkenyl group” is a straight chain or branched chainalkenyl group having a carbon number of 2 to 12, for example, a vinylgroup, an allyl group, an isopropenyl group, a 1-butenyl group, a2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenylgroup, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group,a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, anundecenyl group, a dodecenyl group and the like. The “(C₂-C₁₂)alkynylgroup” is a straight chain or branched chain alkynyl group having acarbon number of 2 to 12, for example, an ethynyl group, a 1-propynylgroup, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a3-butynyl group, a 3-methyl-1-propynyl group, a 2-methyl-3-propynylgroup, a pentynyl group, a 1-hexynyl group, a heptynyl group, an octynylgroup, a nonynyl group, a decynyl group, an undecynyl group, a dodecynylgroup and the like.

The “(C₃-C₆)cycloalkyl group” is a cyclic alkyl group having a carbonnumber of 3 to 6 and is, for example, a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group and the like. The“(C₃-C₇)cycloalkyl group (said cycloalkyl group is optionally fused witha benzene ring)” is a cyclic alkyl group having a carbon number of 3 to7, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl and the like, or a group wherein saidcyclic alkyl group is fused with a benzene ring (e.g., an indan-1-ylgroup, a 1,2,3,4-tetrahydronaphthalen-1-yl group etc.). Examples of the“(C₁-C₆)alkoxy group” include a straight chain or branched chain alkoxygroup having a carbon number of 1 to 6 such as a methoxy group, anethoxy group, a normal propoxy group, an isopropoxy group, a normalbutoxy group, a secondary butoxy group, a tertiary butoxy group, anormal pentyloxy group, an isopentyloxy group, a tertiary pentyloxygroup, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxygroup, an isohexyloxy group, a 1,1,2-trimethylpropyloxy group and thelike. Examples of the “(C₂-C₆)alkenyloxy group” include a straight chainor branched chain alkenyloxy group having a carbon number of 2 to 6 suchas a propenyloxy group, a butenyloxy group, a pentenyloxy group and thelike. Examples of the “(C₂-C₆)alkynyloxy group” include a straight chainor branched chain alkynyloxy group having a carbon number of 2 to 6 suchas a propynyloxy group, a butynyloxy group, a pentynyloxy group and thelike.

The “(C₃-C₁₂)cycloalkyl group” is a cyclic alkyl group having a carbonnumber of 3 to 12, for example, a cyclopropyl group, a cyclobutyl group,a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, a cyclononyl group, a cyclodecyl group, a cycloundecylgroup, a cyclododecyl group and the like. Examples of the“(C₁-C₁₂)alkoxy group” include a straight chain or branched chain alkoxygroup having a carbon number of 1 to 12 such as a methoxy group, anethoxy group, a normal propoxy group, an isopropoxy group, a normalbutoxy group, a secondary butoxy group, a tertiary butoxy group, anormal pentyloxy group, an isopentyloxy group, a tertiary pentyloxygroup, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxygroup, an isohexyloxy group, a 1,1,2-trimethylpropyloxy group, aheptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group,an undecyloxy group, a dodecyloxy group and the like. Examples of the“(C₂-C₁₂)alkenyloxy group” include a straight chain or branched chainalkenyloxy group having a carbon number of 2 to 12 such as a propenyloxygroup, a butenyloxy group, a pentenyloxy group, a hexenyloxy group, aheptenyloxy group, an octenyloxy group, a nonenyloxy group, a decenyloxygroup, an undecenyloxy group, a dodecenyloxy group and the like.Examples of the “(C₂-C₁₂)alkynyloxy group” m include a straight chain orbranched chain alkynyloxy group having a carbon number of 2 to 12 suchas a propynyloxy group, a butynyloxy group, a pentynyloxy group, ahexynyloxy group, a heptynyloxy group, an octynyloxy group, a nonynyloxygroup, a decynyloxy group, an undecynyloxy group, a dodecynyloxy groupand the like.

Examples of the “(C₁-C₆)alkylthio group” include a straight chain orbranched chain alkylthio group having a carbon number of 1 to 6 such asa methylthio group, an ethylthio group, a normal propylthio group, anisopropylthio group, a normal butylthio group, a secondary butylthiogroup, a tertiary butylthio group, a normal pentylthio group, anisopentylthio group, a tertiary pentylthio group, a neopentylthio group,a 2,3-dimethylpropylthio group, a 1-ethylpropylthio group, a1-methylbutylthio group, a normal hexylthio group, an isohexylthiogroup, a 1,1,2-trimethylpropylthio group and the like. Examples of the“(C₁-C₆)alkylsulfinyl group” include a straight chain or branched chainalkylsulfinyl group having a carbon number of 1 to 6 such as amethylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinylgroup, an isopropylsulfinyl group, a normal butylsulfinyl group, asecondary butylsulfinyl group, a tertiary butylsulfinyl group, a normalpentylsulfinyl group, an isopentylsulfinyl group, a tertiarypentylsulfinyl group, a neopentylsulfinyl group, a2,3-dimethylpropylsulfinyl group, a 1-ethylpropylsulfinyl group, a1-methylbutylsulfinyl group, a normal hexylsulfinyl group, anisohexylsulfinyl group, a 1,1,2-trimethylpropylsulfinyl group and thelike. Examples of the “(C₁-C₆)alkylsulfonyl group” include a straightchain or branched chain alkylsulfonyl group having a carbon number of 1to 6 such as a methylsulfonyl group, an ethylsulfonyl group, a normalpropylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonylgroup, a secondary butylsulfonyl group, a tertiary butylsulfonyl group,a normal pentylsulfonyl group, an isopentylsulfonyl group, a tertiarypentylsulfonyl group, a neopentylsulfonyl group, a2,3-dimethylpropylsulfonyl group, a 1-ethylpropylsulfonyl group, a1-methylbutylsulfonyl group, a normal hexylsulfonyl group, anisohexylsulfonyl group, a 1,1,2-trimethylpropylsulfonyl group and thelike.

Examples of the “(C₁-C₁₂)alkylthio group” include a straight chain orbranched chain alkylthio group having a carbon number of 1 to 12 such asa methylthio group, an ethylthio group, a normal propylthio group, anisopropylthio group, a normal butylthio group, a secondary butylthiogroup, a tertiary butylthio group, a normal pentylthio group, anisopentylthio group, a tertiary pentylthio group, a neopentylthio group,a 2,3-dimethylpropylthio group, a 1-ethylpropylthio group, a1-methylbutylthio group, a normal hexylthio group, an isohexylthiogroup, a 1,1,2-trimethylpropylthio group, a heptylthio group, anoctylthio group, a nonylthio group, a decylthio group, an undecylthiogroup, a dodecylthio group and the like. Examples of the“(C₁-C₁₂)alkylsulfinyl group” include a straight chain or branched chainalkylsulfinyl group having a carbon number of 1 to 12 such as amethylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinylgroup, an isopropylsulfinyl group, a normal butylsulfinyl group, asecondary butylsulfinyl group, a tertiary butylsulfinyl group, a normalpentylsulfinyl group, an isopentylsulfinyl group, a tertiarypentylsulfinyl group, a neopentylsulfinyl group, a2,3-dimethylpropylsulfinyl group, a 1-ethylpropylsulfinyl group, a1-methylbutylsulfinyl group, a normal hexylsulfinyl group, anisohexylsulfinyl group, a 1,1,2-trimethylpropylsulfinyl group, aheptylsulfinyl group, an octylsulfinyl group, a nonylsulfinyl group, adecylsulfinyl group, an undecylsulfinyl group, a dodecylsulfinyl groupand the like. Examples of the “(C₁-C₁₂)alkylsulfonyl group” include astraight chain or branched chain alkylsulfonyl group having a carbonnumber of 1 to 12 such as a methylsulfonyl group, an ethylsulfonylgroup, a normal propylsulfonyl group, an isopropylsulfonyl group, anormal butylsulfonyl group, a secondary butylsulfonyl group, a tertiarybutylsulfonyl group, a normal pentylsulfonyl group, an isopentylsulfonylgroup, a tertiary pentylsulfonyl group, a neopentylsulfonyl group, a2,3-dimethylpropylsulfonyl group, a 1-ethylpropylsulfonyl group, a1-methylbutylsulfonyl group, a normal hexylsulfonyl group, anisohexylsulfonyl group, a 1,1,2-trimethylpropylsulfonyl group, aheptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, adecylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl groupand the like.

Examples of the “(C₂-C₁₂)alkenylthio group” include a straight chain orbranched chain alkenylthio group having a carbon number of 2 to 12 suchas a propenylthio group, a butenylthio group, a pentenylthio group, ahexenylthio group, a heptenylthio group, an octenylthio group, anonenylthio group, a decenylthio group, an undecenylthio group, adodecenylthio group and the like. Examples of the “(C₂-C₁₂)alkynylthiogroup” include a straight chain or branched chain alkynylthio grouphaving a carbon number of 2 to 12 such as a propynylthio group, abutynylthio group, a pentynylthio group, a hexynylthio group, aheptynylthio group, an octynylthio group, a nonynylthio group, adecynylthio group, an undecynylthio group, a dodecynylthio group and thelike.

Examples of the “(C₂-C₁₂)alkenylsulfinyl group” include a straight chainor branched chain alkenylsulfinyl group having a carbon number of 2 to12 such as a propenylsulfinyl group, a butenylsulfinyl group, apentenylsulfinyl group, a hexenylsulfinyl group, a heptenylsulfinylgroup, an octenylsulfinyl group, a nonenylsulfinyl group, adecenylsulfinyl group, an undecenylsulfinyl group, a dodecenylsulfinylgroup and the like. Examples of the “(C₂-C₁₂)alkynylsulfinyl group”include a straight chain or branched chain alkynylsulfinyl group havinga carbon number of 2 to 12 such as a propynylsulfinyl group, abutynylsulfinyl group, a pentynylsulfinyl group, a hexynylsulfinylgroup, a heptynylsulfinyl group, an octynylsulfinyl group, anonynylsulfinyl group, a decynylsulfinyl group, an undecynylsulfinylgroup, a dodecynylsulfinyl group and the like.

Examples of the “(C₂-C₁₂)alkenylsulfonyl group” include a straight chainor branched chain alkenylsulfonyl group having a carbon number of 2 to12 such as a propenylsulfonyl group, a butenylsulfonyl group, apentenylsulfonyl group, a hexenylsulfonyl group, a heptenylsulfonylgroup, an octenylsulfonyl group, a nonenylsulfonyl group, adecenylsulfonyl group, an undecenylsulfonyl group, a dodecenylsulfonylgroup and the like. Examples of the “(C₂-C₁₂)alkynylsulfonyl group”include a straight chain or branched chain alkynylsulfonyl group havinga carbon number of 2 to 12 such as a propynylsulfonyl group, abutynylsulfonyl group, a pentynylsulfonyl group, a hexynylsulfonylgroup, a heptynylsulfonyl group, an octynylsulfonyl group, anonynylsulfonyl group, a decynylsulfonyl group, an undecynylsulfonylgroup, a dodecynylsulfonyl group and the like.

Examples of the “(C₃-C₆)cycloalkoxy group” include a cyclic alkoxyhaving a carbon number of 3 to 6 such as a cyclopropoxy group, acyclobutoxy a group, a cyclopentyloxy group, a cyclohexyloxy group andthe like. Examples of the “(C₃-C₁₂)cycloalkyloxy group wherein thecycloalkyl may be fused with a benzene ring” include a cyclic alkoxyhaving a carbon number of 3 to 12 such as a cyclopropoxy group, acyclobutoxy a group, a cyclopentyloxy group, a cyclohexyloxy group, acycloheptyloxy group, a cyclooctyloxy group, a cyclononyloxy group, acyclodecyloxy group, a cycloundecyloxy group, a cyclododecyloxy groupand the like or a group wherein the cyclic alkoxy group is fused with abenzene ring (e.g., indan-1-yloxy group,1,2,3,4-tetrahydronaphthalen-1-yloxy group etc.). Examples of the“(C₃-C₁₂)cycloalkylthio group” include a cyclic alkylthio group having acarbon number of 3 to 12 such as a cyclopropylthio group, acyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, acycloheptylthio group, a cyclooctylthio group, a cyclononylthio group, acyclodecylthio group, a cycloundecylthio group, a cyclododecylthio groupand the like. Examples of the “(C₃-C₁₂)cycloalkylsulfinyl group” includea cyclic alkylsulfinyl group having a carbon number of 3 to 12 such as acyclopropylsulfinyl group, a cyclobutylsulfinyl group, acyclopentylsulfinyl group, a cyclohexylsulfinyl group, acycloheptylsulfinyl group, a cyclooctylsulfinyl group, acyclononylsulfinyl group, a cyclodecylsulfinyl group, acycloundecylsulfinyl group, a cyclododecylsulfinyl group and the like.Examples of the “(C₃-C₁₂)cycloalkylsulfonyl group” include a cyclicalkylsulfonyl group having a carbon number of 3 to 12 such as acyclopropylsulfonyl group, a cyclobutylsulfonyl group, acyclopentylsulfonyl group, a cyclohexylsulfonyl group, acycloheptylsulfonyl group, a cyclooctylsulfonyl group, acyclononylsulfonyl group, a cyclodecylsulfonyl group, acycloundecylsulfonyl group, a cyclododecylsulfonyl group and the like.

In the above-mentioned “(C₁-C₆)alkyl group”, “(C₂-C₆)alkenyl group”,“(C₂-C₆)alkynyl group”, “(C₃-C₆)cycloalkyl group”, “(C₃-C₆)cycloalkoxygroup”, “(C₃-C₁₂)cycloalkyloxy group wherein the cycloalkyl may be fusedwith a benzene ring”, “(C₁-C₆)alkoxy group”, “(C₂-C₆)alkenyloxy group”,“(C₂-C₆)alkynyloxy group”, “(C₁-C₆)alkylthio group”,“(C₁-C₆)alkylsulfinyl group”, “(C₁-C₆)alkylsulfonyl group”,“(C₂-C₁₂)alkenylthio group”, “(C₂-C₁₂)alkynylthio group”,“(C₂-C₁₂)alkenylsulfinyl group”, “(C₂-C₁₂)alkynylsulfinyl group”,“(C₂-C₁₂)alkenylsulfonyl group”, “(C₂-C₁₂)alkynylsulfonyl group”,“(C₁-C₁₂)alkyl group”, “(C₂-C₁₂)alkenyl group”, “(C₂-C₁₂)alkynyl group”,“(C₃-C₁₂)cycloalkyl group”, “(C₁-C₁₂)alkoxy group”, “(C₂-C₁₂)alkenyloxygroup”, “(C₂-C₁₂)alkynyloxy group”, “(C₁-C₁₂)alkylthio group”,“(C₃-C₁₂)cycloalkylthio group”, “(C₁-C₁₂)alkylsulfinyl group”,“(C₃-C₁₂)cycloalkylsulfinyl group”, “(C₁-C₁₂)alkylsulfonyl group” and“(C₃-C₁₂)cycloalkylsulfonyl group”, one or more halogen atoms may besubstituted at substitutable position(s) and, when the number of thesubstituted halogen atoms are two or more, they may be the same ordifferent. They show “halo(C₁-C₆)alkyl group”, “halo(C₂-C₆)alkenylgroup”, “halo(C₂-C₆)alkynyl group”, “halo(C₃-C₆)cycloalkyl group”,“halo(C₃-C₆)cycloalkoxy group”, “halo(C₃-C₁₂)cycloalkyloxy group whereinthe cycloalkyl may be fused with a benzene ring”, “halo(C₁-C₆)alkoxygroup”, “halo(C₂-C₆)alkenyloxy group”, “halo(C₂-C₆)alkynyloxy group”,“halo(C₁-C₆)alkylthio group”, “halo(C₁-C₆)alkylsulfinyl group”,“halo(C₁-C₆)alkylsulfonyl group”, “halo(C₂-C₁₂)alkenylthio group”,“halo(C₂-C₁₂)alkynylthio group”, “halo(C₂-C₁₂)alkenylsulfinyl group”,“halo(C₂₋₁₁₂)alkynylsulfinyl group”, “halo(C₂-C₁₂)alkenylsulfonylgroup”, “halo(C₂-C₁₂)alkynylsulfonyl group”, “halo(C₁-C₁₂)alkyl group”,“halo(C₂-C₁₂)alkenyl group”, “halo(C₂-C₁₂)alkynyl group”,“halo(C₃-C₁₂)cycloalkyl group”, “halo(C₁-C₁₂)alkoxy group”,“halo(C₂₋₁₁₂)alkenyloxy group”, “halo(C₂-C₁₂)alkynyloxy group”,“halo(C₁-C₁₂)alkylthio group”, “halo(C₃-C₁₂)cycloalkylthio group”,“halo(C₁-C₁₂)alkylsulfinyl group”, “halo(C₃-C₁₂)cycloalkylsulfinylgroup”, “halo(C₁-C₁₂)alkylsulfonyl group” and“halo(C₃-C₁₂)cycloalkylsulfonyl group”, respectively.

Examples of the “tri(C₁-C₆)alkylsilyl group” and “tri(C₁-C₁₂)alkylsilylgroup” include a straight chain or branched chain trialkylsilyl grouphaving a carbon number of 1 to 6 or 1 to 12 such as a trimethylsilylgroup, a triethylsilyl group, a tertiary-butyldimethylsilyl group, anethyldimethylsilyl group, an isopropyldimethylsilyl group, ann-propyldimethylsilyl group, and the like. In this case, three alkylgroups may be the same or different.

Examples of the di(C₁-C₁₂)alkylhalo(C₁-C₆)alkylsilyl group include achloromethyldimethylsilyl group and the like. In this case, the twoalkyl groups may be the same or different.

Examples of the di(C₁-C₁₂)alkyl(C₁-C₆)alkylthio(C₁-C₆)alkylsilyl groupinclude a methylthiomethyldimethylsilyl group and the like. In thiscase, the two alkyl groups may be the same or different.

Examples of the di(C₁-C₁₂)alkylhydrosilyl group include adiisopropylsilyl group and the like. In this case, the two alkyl groupsmay be the same or different.

Examples of the di(C₁-C₁₂)alkylhydroxysilyl group include adimethylhydroxysilyl group and the like. In this case, the two alkylgroups may be the same or different.

Examples of the di(C₁-C₁₂)alkylphenylsilyl group include adimethyl(phenyl)silyl group and the like. In this case, the two alkylgroups may be the same or different.

Examples of the di(C₁-C₁₂)alkylbenzylsilyl group include adimethyl(benzyl)silyl group and the like. In this case, the two alkylgroups may be the same or different.

Examples of the “aryl group” include an aromatic hydrocarbon grouphaving a carbon number of 6 to 10 such as a phenyl group, a 1-naphthylgroup, a 2-naphthyl group and the like.

The expressions of “(C₁-C₁₂)”, “(C₂-C₁₂)”, “(C₃-C₁₂)” and the like showranges of the carbon atom numbers of various substituents. Furthermore,the above-mentioned definition applies to the groups wherein theabove-mentioned substituents are bonded to each other. For example,“(C₁-C₆)alkoxy(C₁-C₆)alkyl group” means that a straight chain orbranched chain alkoxy group having a carbon number of 1 to 6 is bondedto a straight chain or branched chain alkyl group having a carbon numberof 1 to 6.

The “(C₃-C₈)alkylene group”, “(C₁-C₆)alkyl(C₃-C₈)alkylene group” and“halo(C₁-C₆)alkylenedioxy group” are groups that can is be formedtogether with the two adjacent X groups, and examples of the“(C₃-C₈)alkylene group” and “(C₁-C₆)alkyl(C₃-C₈)alkylene group” includea propylene group, a butylene group, a pentylene group, a hexylenegroup, a 1,1,4,4-tetramethylbutylene group and the like, and examples ofthe “halo(C₁-C₆)alkylenedioxy group” include a difluoromethylenedioxygroup, a tetrafluoroethylenedioxy group and the like.

Examples of the bicyclo ring formed by X together with the adjacent R²or R³ include bicyclo rings such as 1,2,3,4-tetrahydronaphthalene,inden, indane, 1,2,3,4-tetrahydro-1,4-methanonaphthalene,1,2,3,4-tetrahydro-1,4-ethanonaphthalene and the like. In addition,examples of the fused ring formed by two X groups include fused ringssuch as 2,3-dihydrobenzofuran, 2,3-dihydrobenzothiophene and the like.Examples of the bicyclo ring formed by two adjacent X groups on thearomatic ring include bicyclo rings such as1,2,3,4-tetrahydronaphthalene, inden, indane,1,2,3,4-tetrahydro-1,4-methanonaphthalene,1,2,3,4-tetrahydro-1,4-ethanonaphthalene and the like.

Examples of the “heterocyclic group” and “heterocycle” include a 5- or6-membered monocyclic aromatic heterocyclic group or 3- to 6-memberedmonocyclic nonaromatic heterocyclic group each of which contains, as aring-constituting atom besides carbon atom, 1 to 4 hetero atoms selectedfrom an oxygen atom, a sulfur atom and a nitrogen atom, a fusedheterocyclic group obtained by condensation of the monocyclic aromaticor nonaromatic heterocycle with a benzene ring, and a fused heterocyclicgroup obtained by condensation of the monocyclic aromatic or nonaromaticheterocycles (heterocycles may be different).

Examples of the “aromatic heterocyclic group” include monocyclicaromatic heterocyclic groups such as furanyl, thienyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl,thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl,thiadiazolyl, triazolyl, tetrazolyl, triazinyl and the like; aromaticfused heterocyclic groups such as quinolyl, isoquinolyl, quinazolyl,quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzoisoxazolyl,benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, indazolyl,pyrrolopyrazinyl, imidazopyridinyl, imidazopyrazinyl, pyrazolopyridinyl,pyrazolothienyl, pyrazolotriazinyl and the like.

Examples of the “nonaromatic heterocyclic group” include monocyclicnonaromatic heterocyclic groups such as oxiranyl, thiiranyl, aziridinyl,oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl,thiomorpholinyl, piperazinyl, hexamethyleniminyl, oxazolidinyl,thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, imidazolinyl,dioxolyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-1,3-oxazolidin-5-yl,pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl,1-oxidotetrahydrothiopyranyl, 1,1-dioxidotetrahydrothiopyranyl,tetrahydrofuranyl, dioxanyl, pyrazolidinyl, pyrazolinyl,tetrahydropyrimidinyl, dihydrotriazolyl, tetrahydrotriazolyl and thelike; nonaromatic fused heterocyclic groups such as dihydroindolyl,dihydroisoindolyl, dihydrobenzofuranyl, dihydrobenzodioxinyl,dihydrobenzodioxepinyl, tetrahydrobenzofuranyl, chromenyl,dihydroquinolinyl, tetrahydroquinolinyl, dihydroisoquinolinyl,tetrahydroisoquinolinyl, dihydrophthalazinyl and the like; and the like.

Preferable examples of the “heterocyclic group” include isoquinolinyl,tetrazolyl, quinolinyl, furanyl, tetrahydrofuranyl, isoxazolyl,pyrimidinyl, pyrazinyl, pyridyl, pyrazolyl, benzimidazolyl,2,3-dioxaisoindolyl, tetrahydrofuranyl, oxiranyl, thienyl, pyridazinyland the like.

Examples of the salts of the benzyloxypyrimidine derivative representedby the formula (I) of the present invention include inorganic acid saltssuch as hydrochloride, sulfate, nitrate salt, phosphate and the like,organic acid salts such as acetate, fumarate, maleate, oxalate,methanesulfonate, benzenesulfonate, paratoluenesulfonate and the like,and salts with inorganic or organic bases such as sodium ion, potassiumion, calcium ion, trimethylammonium and the like.

The benzyloxypyrimidine derivative represented by the formula (I) and asalt thereof of the present invention may contain one or plural numberof asymmetric centers in the structural formula, and in some cases, twoor more optical isomers and diastereomers may be present. The presentinvention encompasses any of such optical isomers and mixturescontaining them at any ratio. In addition, the benzyloxypyrimidinederivative represented by the formula (I) and a salt thereof of thepresent invention may have two types of geometric isomers derived from aC—C double bond in the structural formula. The present inventionencompasses all of geometric isomers and the mixtures containing them atany ratio.

Preferred as R¹ is

-   (a1) a hydrogen atom;-   (a2) a (C₁-C₆)alkyl group;-   (a3) a (C₃-C₇)cycloalkyl group (said cycloalkyl group is optionally    fused with a benzene ring);-   (a4) a (C₂-C₆)alkenyl group;-   (a5) a (C₂-C₆)alkynyl group;-   (a6) a halo(C₁-C₆)alkyl group;-   (a8) a halo(C₂-C₆)alkenyl group;-   (a10) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (a11) a (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (a12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group;-   (a13) a (C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group;-   (a14) a (C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group;-   (a16) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;-   (a22) an aryl(C₁-C₆)alkyl group;-   (a23) an aryl(C₁-C₆)alkyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined in the above-mentioned [1];-   (a24) a cyano(C₁-C₆)alkyl group;-   (a30) an aryl group;-   (a31) an aryl group having, on the ring, the same or different 1 to    5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkyl    group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h)    a halo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (j) a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio    group, (l) a (C₁-C₆)alkylsulfinyl group, (m) a    halo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl    group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a    (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) a phenoxy group;-   (a32) an arylsulfonyl group;-   (a33) an arylsulfonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a34) an arylcarbonyl group;-   (a35) an arylcarbonyl group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group    wherein R⁴ and R⁵ are as defined above;-   (a44) a (C₁-C₆)alkylcarbonyl group;-   (a52) a heterocyclic group;-   (a53) a heterocyclic group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) an oxo group;-   (a54) a heterocyclyl(C₁-C₆)alkyl group;-   (a55) a heterocyclyl(C₁-C₆)alkyl group having, on the ring, the same    or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, and (t) an oxo group;-   (a56) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl    groups of the tri(C₁-C₆)alkylsilyl may be the same or different; or-   (a57) a R⁴(R⁵)NCO group wherein R⁴ and R⁵ are as defined above.

Preferred as A is —O—, —S—, —SO— or —SO₂—, more preferably —O— or —S—,further preferably —O—.

R² and R³ may be the same or different and each is preferably

-   (b1) a hydrogen atom;-   (b2) a (C₁-C₆)alkyl group;-   (b3) a (C₃-C₆)cycloalkyl group;-   (b6) a halo(C₁-C₆)alkyl group;-   (b11) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group;-   (b12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; or-   (b13) a (C₁-C₆)alkoxycarbonyl group.

X may be the same or different and each is preferably

-   (c1) a hydrogen atom;-   (c2) a halogen atom;-   (c5) a nitro group;-   (c14) a (C₁-C₁₂)alkyl group;-   (c17) a (C₃-C₁₂)cycloalkyl group;-   (c18) a halo(C₁-C₁₂)alkyl group;-   (c21) a halo(C₃-C₁₂)cycloalkyl group;-   (c22) a tri(C₁-C₁₂)alkylsilyl group wherein the alkyl groups may be    the same or different;-   (c27) a (C₁-C₁₂)alkoxy group;-   (c30) a (C₃-C₁₂)cycloalkyloxy group (said cycloalkyl is optionally    fused with a benzene ring);-   (c31) a halo(C₁-C₁₂)alkoxy group;-   (c38) a halo(C₁-C₆)alkoxy(C₁-C₆)alkoxy group;-   (c42) a (C₁-C₁₂)alkylthio group;-   (c46) a halo(C₁-C₁₂)alkylthio group;-   (c56) a (C₁-C₁₂)alkylsulfinyl group;-   (c66) a (C₁-C₁₂)alkylsulfonyl group;-   (c80) an aryloxy group;-   (c81) an aryloxy group having, on the ring, the same or different 1    to 5 substituents selected from (a) a halogen atom, (b) a cyano    group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a    halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) a    halo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) a    halo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) a    halo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) a    halo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy    group, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a    (C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a    (C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl    group, (t) a (C₁-C₆)alkylsulfonyl group, (u) a    halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and    R⁵ are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵    are as defined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are    as defined above, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as    defined above, (z) a COR⁴ group wherein R⁴ is as defined above, (aa)    a CO₂R⁴ group wherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group    wherein R⁴ and R⁵ are as defined above, and (cc) a C(R⁴)NOR⁵ group    wherein R⁴ and R⁵ are as defined above;-   (c112) a heterocyclic group;-   (c113) a heterocyclic group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c114) a heterocyclyloxy group;-   (c115) a heterocyclyloxy group having, on the ring, the same or    different 1 to 5 substituents selected from (a) a halogen atom, (b)    a cyano group, (c) a nitro group, (d) a formyl group, (e) a    (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₅)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group;-   (c130) a heterocyclyloxy(C₁-C₆)alkyl group; or-   (c131) a heterocyclyloxy(C₁-C₆)alkyl group having, on the ring, the    same or different 1 to 5 substituents selected from (a) a halogen    atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e)    a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a    (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a    (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio    group, (k) a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl    group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a    (C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl    group, (p) a (C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a    (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴    and R⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) a    tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of    the tri(C₁-C₆)alkylsilyl may be the same or different, (v) a    tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups    may be the same or different, and (w) an oxo group, or preferably-   X can form, together with the adjacent R² or R³, (C132) a bicyclo    ring, wherein the bicyclo ring optionally has the same or different,    one or more substituents selected from (a) a halogen atom, (b) a    (C₁-C₆)alkyl group, (c) a halo(C₁-C₆)alkyl group, (d) a    (C₁-C₆)alkoxy group, (e) a halo(C₁-C₆)alkoxy group, (f) a    (C₁-C₆)alkylthio group, (g) a halo(C₁-C₆)alkylthio group, (h) a    (C₁-C₆)alkylsulfinyl group, (i) a halo(C₁-C₆)alkylsulfinyl    group, (j) a (C₁-C₆)alkylsulfonyl group, and (k) a    halo(C₁-C₆)alkylsulfonyl group; or-   X can form, together with the adjacent X on the aromatic ring,    (C133) a bicyclo ring or (C134) a fused ring, wherein the bicyclo    ring or fused ring optionally has the same or different one or more    substituents selected from (a) a halogen atom, (b) a (C₁-C₆)alkyl    group, (c) a halo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxy group, (e)    a halo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g) a    halo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) a    halo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group,    and (k) a halo(C₁-C₆)alkylsulfonyl group.

Preferred as m is 1, 2 or 3, more preferably 1.

Representative production methods of the benzyloxypyrimidine derivativerepresented by the formula (I) of the present invention are shown in thefollowing, to which the present invention is not limited.

Production Method 1.

wherein R¹, R², R³, A, X and m are defined above, and Y is a leavinggroup such as a chlorine atom, a bromine atom, an iodine atom and thelike.

A pyrimidine compound represented by the formula (III) and a compoundrepresented by the formula (II) are reacted in the presence of a base inan inert solvent to give the benzyloxypyrimidine derivative of thepresent invention represented by the formula (I).

The compound represented by the formula (III) can be produced accordingto the method described in Journal of the Chemical Society (1960), 4590,or JP-A-49-92080. In addition, as the starting compound represented bythe formula (II), a product on the market may be directly used.Alternatively, the compound can be produced according to the methoddescribed in a known document (e.g., 4th Edition Jikken Kagaku Kouza 24,The Chemical Society of Japan ed.) or a method analogous thereto.

From Formula (III) to Formula (I)

A pyrimidine compound represented by the formula (III) and a compoundrepresented by the formula (II) are reacted in the presence of a base inan inert solvent to give a pyrimidine derivative represented by theformula (I).

Examples of the base usable for this reaction include inorganic basessuch as sodium hydroxide, potassium hydroxide, sodium carbonate,potassium carbonate, cesium carbonate, sodium hydrogen carbonate,potassium hydrogen carbonate and the like, alkali metal hydrides such assodium hydride, potassium hydride and the like, alkoxides such as sodiummethoxide, sodium ethoxide, potassium tertiary butoxide and the like.

The amount of the base to be used is generally about 1.0- to 5-fold molrelative to a compound represented by the formula (II).

The inert solvent usable in the present reaction may be any as long asit does not markedly inhibit this reaction and, for example, alcoholssuch as methanol, ethanol, propanol, butanol, 2-propanol and the like;chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxaneand the like; aromatic hydrocarbons such as benzene, toluene, xylene andthe like; halogenated hydrocarbons such as methylene chloride,chloroform, carbon tetrachloride and the like, halogenated aromatichydrocarbons such as chlorobenzene, dichlorobenzene and the like;nitriles such as acetonitrile and the like; esters such as ethyl acetateand the like; polar solvents such as N,N-dimethylformamide,N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinoneand the like can be mentioned. These inert solvents may be used alone orin a mixture of two or more kinds thereof.

The reaction temperature in this reaction may be generally from about20° C. to the boiling point of the solvent to be used. While thereaction time varies depending on the reaction scale, reactiontemperature and the like, it can be appropriately selected from therange of several min to 48 hrs.

A compound represented by the formula (II) is used within the range ofgenerally about 1.0- to 5-fold mol relative to a pyrimidine compoundrepresented by the formula (III).

This reaction is also preferably performed in, for example, an inert gassuch as a nitrogen gas and an argon gas.

After completion of the reaction, the objective substance may beisolated from the reaction system containing the objective substance bya conventional method and the objective substance can be produced bypurification using recrystallization or column chromatography, etc., ifnecessary.

Typical examples of the derivative represented by the formula (I) of thepresent invention are shown in Table 1, Table 2, Table 3, Table 4 andTable 5, to which the present invention is not limited.

In the Tables, “Me” is a methyl group, “Et” is an ethyl group, “Pr” is apropyl group, “Bu” is a butyl group, “Pen” is a pentyl group, “Hex” is ahexyl group, “Hep” is a heptyl group, “Ph” is a phenyl group, “TMS” is atrimethylsilyl group, “THF” is a tetrahydrofuranyl group, “Py” is apyridyl group, “furanyl” is a furanyl group, “n-” is normal, “i-” isiso, “s-” is secondary, “neo-” is neo, “t-” is tertiary, and “c-” is analicyclic hydrocarbon group. The “Z” and “E” show configuration ofgeometric isomer. The “substitution position” means the position ofsubstitution in each structural formula, and the property shows amelting point (° C.) or a refractive index n_(D) (measurementtemperature; ° C.).

TABLE 1 compound property No. AR¹ R² R³ (X)_(m) value 1-1 OMe H H 4-t-Bu58-59 1-2 OEt H H 4-t-Bu 1.5368(22.5) 1-3 O—n-Pr H H 4-t-Bu 1.5369(25.0)1-4 O—i-Pr H H 4-t-Bu 59-60 1-5 O—i-Bu H H 4-t-Bu 1.5252(24.5) 1-6O—c-Pen H H 4-t-Bu 1.5392(21.5) 1-7 OCH₂OMe H H 4-t-Bu 54-55 1-8 OCH₂SMeH H 4-t-Bu 1.5666(22.0) 1-9 OCH₂—c-Pr H H 4-t-Bu 1.5440(19.5) 1-10OCH₂CH₂Cl H H 4-t-Bu 1.5490(23.0) 1-11 OCH₂CCl═CH₂ H H 4-t-Bu 1-12OCH₂CH═CHCl(Z) H H 4-t-Bu 1-13 OCH₂CCl═CHCl(E) H H 4-t-Bu 1-14 OPh H H4-t-Bu 1.5710(24.6) 1-15 OMe Me H 4-t-Bu 60-61 1-16 OPh Me H 4-t-Bu1.5661(19.6) 1-17 OMe Et H 4-t-Bu 1-18 OMe i-Pr H 4-t-Bu 130-132 1-19OMe c-Pr H 4-t-Bu 1-20 OMe Me Me 4-t-Bu 64-65 1-21 OMe H H 4-i-Pr1.5548(22.0) 1-22 OEt H H 4-i-Pr 1-23 O—n-Pr H H 4-i-Pr 1.5388(23.0)1-24 O—i-Pr H H 4-i-Pr 1-25 O—c-Pen H H 4-i-Pr 1-26 OCH₂—c-Pr H H 4-i-Pr1.547(26.5) 1-27 OCH₂CH₂Cl H H 4-i-Pr 1-28 OCH₂CCl═CH₂ H H 4-i-Pr1.5540(22.5) 1-29 OCH₂CH═CHCl(Z) H H 4-i-Pr 1-30 OCH₂CCl═CHCl(E) H H4-i-Pr 1.5583(20.5) 1-31 OPh H H 4-i-Pr 1-32 OMe Me H 4-i-Pr 1-33 OMe MeMe 4-i-Pr 1-34 OH H H 4-i-Bu 1-35 OMe H H 4-i-Bu 70-71 1-36 OEt H H4-i-Bu 1-37 O—n-Pr H H 4-i-Bu 1-38 O—i-Pr H H 4-i-Bu 1-39 O—c-Pen H H4-i-Bu 1.5420(20.5) 1-40 OCH₂OMe H H 4-i-Bu 1.5341(23.0) 1-41 OCH₂—c-PrH H 4-i-Bu 1.5434(20.5) 1-42 OCH₂CH₂Cl H H 4-i-Bu 1.5440(20.5) 1-43OCH₂CCl═CH₂ H H 4-i-Bu 1-44 OCH₂CH═CHCl(Z) H H 4-i-Bu 1-45OCH₂CCl═CHCl(E) H H 4-i-Bu 1-46 OPh H H 4-i-Bu 1-47 OMe Me H 4-i-Bu 1-48OMe Me Me 4-i-Bu 1-49 OMe H H 4-neo-Pen 1-50 OEt H H 4-neo-Pen 1-51O—n-Pr H H 4-neo-Pen 1-52 O—i-Pr H H 4-neo-Pen 1-53 O—c-Pen H H4-neo-Pen 1-54 OCH₂—c-Pr H H 4-neo-Pen 1-55 OCH₂CH₂Cl H H 4-neo-Pen 1-56OCH₂CCl═CH₂ H H 4-neo-Pen 1-57 OCH₂CH═CHCl(Z) H H 4-neo-Pen 1-58OCH₂CCl═CHCl(E) H H 4-neo-Pen 1-59 OPh H H 4-neo-Pen 1-60 OMe Me H4-neo-Pen 1-61 OMe Me Me 4-neo-Pen 1-62 OMe H H 4-TMS 72-73 1-63 OEt H H4-TMS 1.5401(22.0) 1-64 O—n-Pr H H 4-TMS 1.5370(23.5) 1-65 O—i-Pr H H4-TMS 1.5183(23.0) 1-66 O—c-Pen H H 4-TMS 1.5388(23.0) 1-67 OCH₂OMe H H4-TMS 1.5360(24.5) 1-68 OCH₂—c-Pr H H 4-TMS 1.5419(23.0) 1-69 OCH₂CH₂ClH H 4-TMS 1.5470(23.0) 1-70 OCH₂CCl═CH₂ H H 4-TMS 1.5479(22.0) 1-71OCH₂CH═CHCl(Z) H H 4-TMS 1-72 OCH₂CCl═CHCl(E) H H 4-TMS 73-74 1-73 OPh HH 4-TMS 1-74 OMe H H 3-Cl-4-TMS 48-49 1-75 OMe H H 2-Cl-4-TMS 1-76 OMeMe H 4-TMS 1.5347(17.4) 1-77 OMe Me Me 4-TMS 1-78 OMe H H 4-CF₃ 57-581-79 OEt H H 4-CF₃ 1-80 O—n-Pr H H 4-CF₃ 45-46 1-81 O—i-Pr H H 4-CF₃41-42 1-82 O—c-Pen H H 4-CF₃ 1.5057(23.5) 1-83 OCH₂OMe H H 4-CF₃ 60-611-84 OCH₂SMe H H 4-CF₃ 46-47 1-85 OCH₂SOMe H H 4-CF₃ 113-114 1-86OCH₂C≡CH H H 4-CF₃ 87-88 1-87 OCH₂—c-Pr H H 4-CF₃ 45-46 1-88 OCH₂CH₂F HH 4-CF₃ 52-53 1-89 OCH₂CH₂Cl H H 4-CF₃ 48-49 1-90 OCH₂CH═CH₂ H H 4-CF₃1.5153(26.0) 1-91 OCH₂CCl═CH₂ H H 4-CF₃ 1.5240(23.5) 1-92 OCH₂CH═CHCl(Z)H H 4-CF₃ 61-62 1-93 OCH₂CCl═CHCl(E) H H 4-CF₃ 78-79 1-94 OCH₂Ph H H4-CF₃ 48-49 1-95 OPh H H 4-CF₃ 56-57 1-96 OMe Me H 4-CF₃ 1.5093(22.5)1-97 OMe Me Me 4-CF₃ 1.5190(23.0) 1-98 OMe H H 3-CF₃ 63-64 1-99 OMe H H2-CF₃ 31-32 1-100 OCH₂CH═CCl₂ H H 4-CF₃ 66-67 1-101 OMe i-Bu H 4-CF₃76-78 1-102 OCH₂CCl═CHCl(Z) H H 4-CF₃ 1.5268(23.5) 1-103 OMe H H 4-OCF₃75-76 1-104 OEt H H 4-OCF₃ 1-105 O—n-Pr H H 4-OCF₃ 1-106 O—i-Pr H H4-OCF₃ 1-107 O—c-Pen H H 4-OCF₃ 41-42 1-108 OCH₂OMe H H 4-OCF₃ 51-521-109 OCH₂—c-Pr H H 4-OCF₃ 62-64 1-110 OCH₂CH₂Cl H H 4-OCF₃ 44-45 1-111OCH₂CCl═CH₂ H H 4-OCF₃ 1-112 OCH₂CH═CHCl(Z) H H 4-OCF₃ 1-113OCH₂CCl═CHCl(E) H H 4-OCF₃ 73-76 1-114 OPh H H 4-OCF₃ 1.5422(16.5) 1-115OCOPh H H 4-OCF₃ 1.5381(21.5) 1-116 OMe Me H 4-OCF₃ 1.4871(21.5) 1-117OCH₂OMe Me H 4-OCF₃ 1.4940(22.5) 1-118 OMe Me Me 4-OCF₃ 1.5053(19.6)1-119 OH H H 4-OCF₂CF₂H 163-164 1-120 OMe H H 4-OCF₂CF₂H 65-66 1-121 OEtH H 4-OCF₂CF₂H 1-122 O—n-Pr H H 4-OCF₂CF₂H 34-35 1-123 O—i-Pr H H4-OCF₂CF₂H 1-124 O—c-Pen H H 4-OCF₂CF₂H 1.5063(21.0) 1-125 OCH₂CF₃ H H4-OCF₂CF₂H 1-126 OCH₂TMS H H 4-OCF₂CF₂H 1-127 OCH₂OMe H H 4-OCF₂CF₂H1.5860(24.5) 1-128 OCH₂C≡CH H H 4-OCF₂CF₂H 1-129 OCH₂—c-Pr H H4-OCF₂CF₂H 54-55 1-130 OCH₂CH₂Cl H H 4-OCF₂CF₂H 1.5115(20.5) 1-131OCH₂CCl═CH₂ H H 4-OCF₂CF₂H 1-132 OCH₂CH═CHCl(Z) H H 4-OCF₂CF₂H 1-133OCH₂CCl═CHCl(E) H H 4-OCF₂CF₂H 1-134 OCH₂Ph H H 4-OCF₂CF₂H 1.5290(22.5)1-135 OPh H H 4-OCF₂CF₂H 1.5364(22.0) 1-136 OMe Me H 4-OCF₂CF₂H 1-137OMe Me Me 4-OCF₂CF₂H 1-138 OMe H H 4-SCF₃ 77-78 1-139 OEt H H 4-SCF₃57-58 1-140 O—n-Pr H H 4-SCF₃ 1-141 O—i-Pr H H 4-SCF₃ 31-32 1-142O—c-Pen H H 4-SCF₃ 47-48 1-143 OCH₂—c-Pr H H 4-SCF₃ 45-46 1-144OCH₂CH₂Cl H H 4-SCF₃ 34-35 1-145 OCH₂CCl═CH₂ H H 4-SCF₃ 1.5440(22.0)1-146 OCH₂CH═CHCl(Z) H H 4-SCF₃ 47-48 1-147 OCH₂CCl═CHCl(E) H H 4-SCF₃62-63 1-148 OPh H H 4-SCF₃ 41-42 1-149 OMe Me H 4-SCF₃ 1-150 OMe Me Me4-SCF₃ 1-151 OMe H H 4-SCF₂CF₃ 1-152 OEt H H 4-SCF₂CF₃ 1-153 O—n-Pr H H4-SCF₂CF₃ 1-154 O—i-Pr H H 4-SCF₂CF₃ 1-155 O—c-Pen H H 4-SCF₂CF₃ 1-156OCH₂—c-Pr H H 4-SCF₂CF₃ 44-45 1-157 OCH₂CH₂Cl H H 4-SCF₂CF₃ 39-40 1-158OCH₂CCl═CH₂ H H 4-SCF₂CF₃ 1-159 OCH₂CH═CHCl(Z) H H 4-SCF₂CF₃ 1-160OCH₂CCl═CHCl(E) H H 4-SCF₂CF₃ 1-161 OPh H H 4-SCF₂CF₃ 1-162 OMe Me H4-SCF₂CF₃ 1-163 OMe Me Me 4-SCF₂CF₃ 1-164 OMe H H 4-SCF(CF₃)₂ 1-165 OEtH H 4-SCF(CF₃)₂ 1-166 O—n-Pr H H 4-SCF(CF₃)₂ 1-167 O—i-Pr H H4-SCF(CF₃)₂ 1-168 O—c-Pen H H 4-SCF(CF₃)₂ 1-169 OCH₂—c-Pr H H4-SCF(CF₃)₂ 1-170 OCH₂CH₂Cl H H 4-SCF(CF₃)₂ 1-171 OCH₂CCl═CH₂ H H4-SCF(CF₃)₂ 1-172 OCH₂CH═CHCl(Z) H H 4-SCF(CF₃)₂ 1-173 OCH₂CCl═CHCl(E) HH 4-SCF(CF₃)₂ 1-174 OPh H H 4-SCF(CF₃)₂ 1-175 OMe Me H 4-SCF(CF₃)₂ 1-176OMe Me Me 4-SCF(CF₃)₂ 1-177 OMe H H 4-CF(CF₃)₂ 1-178 OEt H H 4-CF(CF₃)₂1-179 O—n-Pr H H 4-CF(CF₃)₂ 1-180 O—i-Pr H H 4-CF(CF₃)₂ 1-181 O—c-Pen HH 4-CF(CF₃)₂ 1-182 OCH₂—c-Pr H H 4-CF(CF₃)₂ 1-183 OCH₂CH₂Cl H H4-CF(CF₃)₂ 1-184 OCH₂CCl═CH₂ H H 4-CF(CF₃)₂ 1-185 OCH₂CH═CHCl(Z) H H4-CF(CF₃)₂ 1-186 OCH₂CCl═CHCl(E) H H 4-CF(CF₃)₂ 1-187 OPh H H 4-CF(CF₃)₂1-188 OMe Me H 4-CF(CF₃)₂ 1-189 OMe Me Me 4-CF(CF₃)₂ 1-190 OMe H H 4-F119-120 1-191 OEt H H 4-F 1-192 O—n-Pr H H 4-F 1.5390(21.5) 1-193 O—i-PrH H 4-F 1-194 O—c-Pen H H 4-F 1-195 OCH₂—c-Pr H H 4-F 1.5470(21.0) 1-196OCH₂CH₂Cl H H 4-F 1-197 OCH₂CCl═CH₂ H H 4-F 1-198 OCH₂CH═CHCl(Z) H H 4-F1-199 OCH₂CCl═(E) H H 4-F 1-200 OPh H H 4-F 1-201 OMe Me H 4-F 1-202 OMeMe Me 4-F 1-203 OMe H H 3,4-F₂  99-101 1-204 OMe H H 2-Cl-4-F 101-1021-205 OMe H H 3-OPh 1.5942(23.5) 1-206 OMe H H 4-OPh 1.5995(21.5) 1-207OMe H H 4-Br 117-118 1-208 OMe H H 3-Cl 52-53 1-209 OMe H H 4-Cl 104-1051-210 OMe H H 2,4-Cl₂ 106-107 1-211 OMe H H 3-NO₂-4-Cl 140-141 1-212 OMeH H 4-O—t-Bu 57-58 1-213 OMe H H 4-SMe 73-74 1-214 OMe H H 4-SOMe103-104 1-215 OMe H H 4-SO₂Me 155-156 1-216 OMe H H 2-Cl-4-Br 121-1221-217 OMe H H 3-Cl-4-O—i-Pr 58-59 1-218 OMe Me H 4-OCH₂CF₃ 1.4980(23.0)1-219 OMe H H 4-c-Hex 67-68 1-220 OPh H H 4-Br 1.6136(20.7) 1-221 OMe HH 4-O—c-Pen 58-60 1-222 OMe H H 3,4-Cl₂ 113-114 1-223 OMe H H 4-I115-116 1-224 OMe H H H 31-32 1-225 OMe H H 4-O—c-Hex 64-65 1-226 OMe HH 4-S—i-Pr 73-74 1-227 OMe H H 4-O—i-Pr 1.5536(22.0) 1-228 OCH₂OMe H H4-O—i-Pr 1.5408(22.0) 1-229 OMe H H 3,4,5-(OMe)₃ 88-89 1-230 OMe H H3,4-(OMe)₂ 54-55 1-231 OMe Me Me H 1.5486(22.6) 1-232 OMe Me H 4-O—i-Pr1.5482(22.5) 1-233 OMe H H 3-OMe-4-OEt 76-77 1-234 OMe H H 4-Me 46-471-235 OMe CF₃ H H 86-87 1-236 OMe H H 2,3,4,5,6-F₅ 73-74 1-237 OMe H H2,5-F₂ 104-105 1-238 OMe H H 4-CMe₂CH₂Me 1-239 OMe H H 4-CMe₂CH₂Cl 1-240OMe H H 4-OCF₂H 50-51 1-241 OMe H H 4-SCF₂H 1-242 OMe H H 2-F-4-Cl 99-100 1-243 OMe H H 2-F-4-Br 61-62 1-244 SMe H H 4-t-Bu 1.5449(20.7)1-245 SEt H H 4-t-Bu 1.5502(19.6) 1-246 SMe H H 4-CF₃ 52-53 1-247 SEt HH 4-CF₃ 44-45 1-248 O—n-Bu H H 4-CF₃ 1.4950(21.5) 1-249 O—i-Bu H H 4-CF₃45-46 1-250 O—s-Bu H H 4-CF₃ 1.4965(22.5) 1-251 O-3-Pen H H 4-CF₃1.4959(22.5) 1-252 O-neo-Pen H H 4-CF₃ 57-58 1-253 O—c-Hex H H 4-CF₃1.5048(20.5) 1-254 OCH₂C≡CMe H H 4-CF₃ 74-75 1-255 OMe H H 2-F-4-CF₃1-256 O—n-Pr H H 2-F-4-CF₃ 42-45 1-257 O—i-Bu H H 2-F-4-CF₃ 38-42 1-258O—s-Bu H H 2-F-4-CF₃ 1.492(21.5) 1-259 O—c-Pen H H 2-F-4-CF₃ 1.508(26.5)1-260 OCH₂—c-Pr H H 2-F-4-CF₃ 35-36 1-261 OPh H H 2-F-4-CF₃ 65-66 1-262OMe H H 2-Cl-4-CF₃ 1-263 O—n-Pr H H 2-Cl-4-CF₃ 1-264 O—i-Bu H H2-Cl-4-CF₃ 57-59 1-265 O—s-Bu H H 2-Cl-4-CF₃ 1.509(30.0) 1-266 OCH₂—c-PrH H 2-Cl-4-CF₃ 51-53 1-267 OMe H H 2-OMe-4-CF₃  99-100 1-268 O—i-Bu H H2-OMe-4-CF₃ 1-269 O—s-Bu H H 2-OMe-4-CF₃ 1-270 OMe H H 2-NO₂-4-CF₃123-126 1-271 OMe H H 2-F-4-OCHF₂ 1-272 O—i-Bu H H 2-F-4-OCHF₂ 1-273O—s-Bu H H 2-F-4-OCHF₂ 1-274 OMe H H 2-F-4-OCF₃ 1-275 O—i-Bu H H2-F-4-OCF₃ 1-276 O—s-Bu H H 2-F-4-OCF₃ 1-277 OMe H H 2-F-4- OCF₂CF₂H1-278 O—i-Bu H H 2-F-4- OCF₂CF₂H 1-279 O—s-Bu H H 2-F-4- OCF₂CF₂H 1-280OMe H H 2-F-4-OCH₂CF₃ 1-281 O—i-Bu H H 2-F-4-OCH₂CF₃ 1-282 O—s-Bu H H2-F-4-OCH₂CF₃ 1.4918(27.6) 1-283 OMe H H 2-F-4- OCH₂CH₂F 1-284 O—i-Bu HH 2-F-4- OCH₂CH₂F 1-285 O—s-Bu H H 2-F-4- OCH₂CH₂F 1-286 OMe H H2-F-4-O—i-Pr 1-287 O—i-Bu H H 2-F-4-O—i-Pr 1-288 O—s-Bu H H 2-F-4-O—i-Pr1-289 O—s-Bu(R FORM) H H 4-CF₃ 1.5000(24.5) 1-290 O—s-Bu(S FORM) H H4-CF₃ 1.5000(24.5) 1-291 O—s-Bu(R FORM) H H 4-t-Bu 1-292 O—s-Bu(S FORM)H H 4-t-Bu 1-293 O—s-Bu(R FORM) H H 4-TMS 1-294 O—s-Bu(S FORM) H H 4-TMS

TABLE 2 compound property No. AR¹ Z value 2-1 OMe

125-126 2-2 OMe

113-114 2-3 OMe

 98-99 2-4 OMe

1.5518 (22.6) 2-5 OMe

121-123 2-6 O—n-Pr

1.5718 (25.5) 2-7 O—s-Bu

1.3361 (23.7) 2-8 O—s-Bu

 70-71

TABLE 3 property compound No. AR¹ R² R³ (X)_(m) value 3-1 O—n-Bu H H4-t-Bu 1.5268 (22.5) 3-2 O—s-Bu H H 4-t-Bu  40-41 3-3 O—n-Pen H H 4-t-Bu1.5277 (23.0) 3-4 O-3-Pen H H 4-t-Bu NMR 3-5 OCHMe—n-Pr H H 4-t-Bu1.5219 (20.5) 3-6 OCHMe—c-Pr H H 4-t-Bu 1.5295 (22.5) 3-7 OCH₂CH═CH₂ H H4-t-Bu 1.5400 (26.0) 3-8 O-2-THF H H 4-t-Bu  48-49 3-9 OCH₂CH₂F H H4-t-Bu  66-67 3-10 OCH₂CHF₂ H H 4-t-Bu 1.3789 (17.1) 3-11 OCH₂CF₃ H H4-t-Bu 1.5089 (21.0) 3-12 OCH₂CH₂CF₃ H H 4-t-Bu  55-56 3-13 OCH₂CF₂CHF₂H H 4-t-Bu 1.3806 (22.7) 3-14 OCH₂CF₂CF₃ H H 4-t-Bu 1.5007 (22.7) 3-15OCH₂CH₂CH₂F H H 4-t-Bu  62-63 3-16 OSO₂-4-Me—Ph H H 4-t-Bu 1.3445 (21.3)3-17 OCH₂Ph H H 4-t-Bu 1.4780 (22.2) 3-18 O-2-Cl—Ph H H 4-t-Bu 1.5728(26.0) 3-19 O-2-F—Ph H H 4-t-Bu 1.3945 (25.2) 3-20 O-2-Me—Ph H H 4-t-Bu1.5683 (23.0) 3-21 O-2-OMe—Ph H H 4-t-Bu  83-84 3-22 O-2,4-F₂—Ph H H4-t-Bu 1.4028 (22.1) 3-23 O-2,6-F₂—Ph H H 4-t-Bu 1.3668 (20.7) 3-24OCH₂OMe CF₃ H 4-t-Bu 1.4941 (17.5) 3-25 O—i-Pr CF₃ H 4-t-Bu 1.4921(18.0) 3-26 O—c-Pen CF₃ H 4-t-Bu 1.5054 (17.0) 3-27 OMe H H 2-OEt-4-t-Bu 38-43 3-28 OMe H H 2-OMe-4-t-Bu  99-101 3-29 O—n-Bu H H 4-i-Pr 1.5380(28.5) 3-30 O—i-Bu H H 4-i-Pr 1.5310 (24.5) 3-31 O—s-Bu H H 4-i-Pr1.5310 (24.5) 3-32 O—c-Pen H H 4-i-Pr 1.5440 (26.5) 3-33 OCH₂OMe H H4-i-Pr 1.5350 (24.5) 3-34 OCH₂CMe═CH₂ H H 4-i-Pr 1.5438 (22.5) 3-35O-2-F—Ph H H 4-i-Pr 1.4017 (22.2) 3-36 O-2,4-F₂—Ph H H 4-i-Pr 1.4162(22.0) 3-37 O—i-Bu H H 4-TMS  49-50 3-38 O—s-Bu H H 4-TMS 1.5209 (21.0)3-39 O—neo-Pen H H 4-TMS 1.5203 (22.0) 3-40 OCH₂CF₃ H H 4-TMS 1.5080(22.0) 3-41 OCH₂CH₂F H H 4-TMS 1.5395 (22.0) 3-42 OCH₂CH₂OMe H H 4-TMS1.3370 (22.0) 3-43 OCHMeCH₂Cl H H 4-TMS  42-43 3-44 OCHMe—n-Pr H H 4-TMS1.5290 (21.0) 3-45 OCH₂CMe═CH₂ H H 4-TMS 1.5400 (22.0) 3-46 OCH₂CCl═CHCl(Z) H H 4-TMS 1.5540 (22.0) 3-47 OCH₂-2-furanyl H H 4-TMS 1.5261 (22.0)3-48 OCH₂-2-Py H H 4-TMS  73-74 3-49 OCH₂-3-Py H H 4-TMS  49-50 3-50OCH₂-4-Py H H 4-TMS  53-54 3-51 O-2-F—Ph H H 4-TMS 3-52 OCONMe₂ H H4-TMS 1.5157 (22.0) 3-53 OCONEt₂ H H 4-TMS 1.5270 (21.5) 3-54 O—c-Bu H H4-CF₃  55-56 3-55 O—c-Hep H H 4-CF₃ 1.5139 (20.5) 3-56 OCHMe—n-Pr H H4-CF₃ 1.4980 (20.5) 3-57 OCHMe—i-Pr H H 4-CF₃ 1.4971 (22.5) 3-58OCHMe—c-Pr H H 4-CF₃ 1.5038 (22.5) 3-59 OCH₂—c-Pen H H 4-CF₃  42-43 3-60OCH₂—c-Hex H H 4-CF₃  42-43 3-61 OCH₂CHMeEt H H 4-CF₃ 1.4986 (20.5) 3-62OCHMeCH₂Cl H H 4-CF₃ 1.5125 (21.0) 3-63 OCH₂SO₂Me H H 4-CF₃  90-91 3-64OCH₂OEt H H 4-CF₃  49-50 3-65 OCH₂CN H H 4-CF₃  72-73 3-66 OCH₂TMS H H4-CF₃  50-52 3-67 OCH₂CH₂OMe H H 4-CF₃ 1.5084 (23.0) 3-68 OCH₂CH₂Ph H H4-CF₃ 1.5398 (22.0) 3-69

H H 4-CF₃ 1.5271 (21.0) 3-70

H H 4-CF₃  51-52 3-71 OCH₂CH═CHCl (E) H H 4-CF₃  98-99 3-72 OCH₂CH═CHMe(E) H H 4-CF₃  60-61 3-73 OCHMeCH═CH₂ H H 4-CF₃ 1.5021 (22.5) 3-74OCH₂CMe═CH₂ H H 4-CF₃  33-34 3-75 OC(Me)₂CH═CH₂ H H 4-CF₃ 1.5005 (21.5)3-76 OCHMeC≡CH H H 4-CF₃  64-65 3-77 OC(Me)₂C≡CH H H 4-CF₃  49-50 3-78O-2-THF H H 4-CF₃ 1.5132 (26.0) 3-79 O-3-THF H H 4-CF₃  76-77 3-80OCH₂CF₂H H H 4-CF₃  54-55 3-81 OCH₂CF₃ H H 4-CF₃ 1.4672 (28.9) 3-82OCH₂CH₂CH₂F H H 4-CF₃  52-54 3-83 OCH₂CH₂CH═CF₂ H H 4-CF₃ 1.3835 (19.0)3-84 OCHMePh H H 4-CF₃ 1.5341 (22.5) 3-85 OCH₂-2-OMe—Ph H H 4-CF₃  81-823-86 OCH₂-4-OMe—Ph H H 4-CF₃ 100-101 3-87 OCH₂-2-F—Ph H H 4-CF₃  73-743-88 OCH₂-3-F—Ph H H 4-CF₃  54-55 3-89 OCH₂-4-F—Ph H H 4-CF₃  41-42 3-90OCH₂-2,6-F₂—Ph H H 4-CF₃  52-53 3-91 O-2-F—Ph H H 4-CF₃ 1.5300 (28.0)3-92 O-3-F—Ph H H 4-CF₃ 1.5232 (28.0) 3-93 O-4-F—Ph H H 4-CF₃ 1.5289(28.6) 3-94 O-2-Cl—Ph H H 4-CF₃  83-84 3-95 O-2-CF₃—Ph H H 4-CF₃  38-403-96 O-2-Me—Ph H H 4-CF₃ 1.5448 (23.0) 3-97 O-2-i-Pr—Ph H H 4-CF₃ 1.5360(24.5) 3-98 O-2-OMe—Ph H H 4-CF₃  52-53 3-99 O-2,4-F₂—Ph H H 4-CF₃ 66-68 3-100 O-2,6-F₂—Ph H H 4-CF₃  85-86 3-101 O-2-Py H H 4-CF₃ 3-102O-3-Cl-5-CF₃-2-Py H H 4-CF₃  72-73 3-103 O-3-CF₃-2-Py H H 4-CF₃ 1.5070(22.5) 3-104 O-5-CF₃-2-Py H H 4-CF₃ 1.5154 (22.5) 3-105 O-6-CF₃-2-Py H H4-CF₃ 1.4879 (22.5) 3-106 O-4-CF₃-2-Py H H 4-CF₃ 1.5086 (22.0) 3-107OCH₂—c-Pr Me H 4-CF₃  55-56 3-108 OMe Et H 4-CF₃  72-73 3-109 OMe c-Pr H4-CF₃  73-74 3-110 OMe c-Pen H 4-CF₃  59-60 3-111 OMe H H 2-F-5-CF₃3-112 O—i-Bu H H 2-F-5-CF₃ 1.4892 (29.5) 3-113 O—s-Bu H H 2-F-5-CF₃1.4886 (29.5) 3-114 OCH₂OMe H H 2-F-5-CF₃  67-68 3-115 OMe H H 3-F-4-CF₃3-116 O—i-Bu H H 3-F-4-CF₃ 3-117 O—s-Bu H H 3-F-4-CF₃ 1.4850 (28.5)3-118 OMe H H 3-CF₃ 3-119 O—i-Bu H H 3-CF₃ 3-120 O—s-Bu H H 3-CF₃ 1.4842(28.6) 3-121 O—i-Bu H H 2-F-3-CF₃ 1.4811 (25.3) 3-122 O—s-Bu H H2-F-3-CF₃ 1.4880 (28.6) 3-123 O—n-Bu H H 4-OCF₃  30-31 3-124 O—i-Bu H H4-OCF₃ 1.4928 (21.5) 3-125 O—s-Bu H H 4-OCF₃ 1.4948 (21.5) 3-126 O—c-HexH H 4-OCF₃ 1.5083 (16.5) 3-127 OCH₂-2-THF H H 4-OCF₃  53-58 3-128OCH₂-2-furanyl H H 4-OCF₃ 1.5281 (19.0) 3-129 OCH₂Ph H H 4-OCF₃  46-493-130 OCH₂CCl═CHCl (Z) H H 4-OCF₃  38-39 3-131 OC(Me)₂C≡CH H H 4-OCF₃1.5025 (22.5) 3-132 O-2-F—Ph H H 4-OCF₃  37-38 3-133 O-2-Cl—Ph H H4-OCF₃ 1.5416 (23.0) 3-134 O-2-Me—Ph H H 4-OCF₃ 1.5354 (24.6) 3-135O-2-OMe—Ph H H 4-OCF₃ 1.5382 (24.6) 3-136 O—s-Bu H H 3-F-4-OCF₃ 1.4802(28.8) 3-137 OCOMe H H 4-OCF₂CF₂H 1.4911 (22.5) 3-138 OCHMePh H H4-OCF₂CF₂H 1.5352 (22.5) 3-139 O—i-Bu H H 4-SCF₃  40-41 3-140 O—s-Bu H H4-SCF₃  32-33 3-141 OCH₂-2-THF H H 4-SCF₃ 1.5382 (22.0) 3-142 OCH₂OMe HH 4-SCF₃  57-58 3-143 OCH₂CH₂F H H 4-SCF₃  62-63 3-144 OCH₂Ph H H 4-SCF₃ 52-53 3-145 OCH₂OMe H H 4-SCF₂CF₃  43-44 3-146 O—i-Bu H H 4-F  38-393-147 O—s-Bu H H 4-F 1.524 (21.5) 3-148 OCH₂OMe H H 4-F  54-57 3-149 OMeH H 2-F 3-150 O—n-Pr H H 2-F 3-151 O—i-Bu H H 2-F 3-152 O—s-Bu H H 2-F1.5242 (28.0) 3-153 OMe H H 2,4-F₂ 105-106 3-154 O—n-Pr H H 2,4-F₂1.5260 (21.0) 3-155 O—i-Pr H H 2,4-F₂ 3-156 O—i-Bu H H 2,4-F₂ 1.516(26.5) 3-157 O—s-Bu H H 2,4-F₂ 1.516 (26.5) 3-158 OCH₂OMe H H 2,4-F₂ 55-58 3-159 OPh H H 2,4-F₂  45-46 3-160 OMe H H 2,6-F₂ 3-161 O—n-Pr H H2,6-F₂ 3-162 O—i-Pr H H 2,6-F₂ 3-163 O—i-Bu H H 2,6-F₂ 3-164 O—s-Bu H H2,6-F₂ 1.5150 (28.0) 3-165 OMe H H H 3-166 O—n-Pr H H H 3-167 O—i-Bu H HH 3-168 O—s-Bu H H H 1.5352 (27.5) 3-169 OMe Me H H 1.5622 (17.8) 3-170OMe c-Pr H H  71-72 3-171 OCH₂OMe CF₃ H H 1.4870 (17.5) 3-172 O—c-PenCF₃ H H 1.5110 (17.5) 3-173 OCH₂CCl═CHCl (Z) CF₃ H H 1.5323 (17.5) 3-174OCH₂CCl═CHCl (E) CF₃ H H 1.5294 (17.5) 3-175 OPh CF₃ H H 1.5436 (19.0)3-176 OC(Me)₂C≡CH CF₃ H H 1.4720 (22.5) 3-177 OMe CO₂Me H H 113-1143-178 OMe CH₂OMe H H 1.5549 (20.0) 3-179 O—n-Pr H H 4-Cl  34-35 3-180O—i-Pr H H 4-Cl  55-56 3-181 O—i-Bu H H 4-Cl 1.5490 (20.5) 3-182 O—s-BuH H 4-Cl 1.5506 (20.5) 3-183 OCH₂—c-Pr H H 4-Cl  42-43 3-184 OCH₂OMe H H4-Cl  71-72 3-185 O—n-Pr Me H 4-Cl 1.5533 (20.6) 3-186 OPh CF₃ H 4-Cl1.5483 (18.0) 3-187 OMe CF₃ H 4-Cl  76-77 3-188 OCH₂OMe CF₃ H 4-Cl1.5141 (22.0) 3-189 OMe CH₂SMe H 4-Cl 1.5881 (22.5) 3-190 O—n-Pr H H2,4-Cl₂  62-64 3-191 O—s-Bu H H 4-Br 1.5650 (21.0) 3-192 O—s-Bu H H 4-I 49-50 3-193 OEt H H 4-OCF₂H 3-194 O—n-Pr H H 4-OCF₂H 1.5202 (20.5)3-195 O—i-Pr H H 4-OCF₂H 3-196 O—i-Bu H H 4-OCF₂H 3-197 O—s-Bu H H4-OCF₂H 3-198 OMe H H 4-Me 3-199 O—n-Pr H H 4-Me 1.5418 (28.5) 3-200O—i-Pr H H 4-Me 3-201 O—i-Bu H H 4-Me 3-202 O—s-Bu H H 4-Me 3-203 OMe HH 4-SMe 3-204 O—n-Pr H H 4-SMe 3-205 O—i-Bu H H 4-SMe 3-206 O—s-Bu H H4-SMe 1.5720 (28.5) 3-207 O—s-Bu H H 4-s-Bu 1.5252 (27.5) 3-208 O—s-Bu HH 4-SO₂Me 1.5513 (27.5) 3-209 O—i-Bu H H 4-CMe₂Et 1.5250 (27.5) 3-210OMe H H 4-OCH₂CF₃ 3-211 O—n-Pr H H 4-OCH₂CF₃  37-38 3-212 O—i-Pr H H4-OCH₂CF₃ 3-213 O—i-Bu H H 4-OCH₂CF₃  31-32 3-214 O—s-Bu H H 4-OCH₂CF₃1.4972 (28.7) 3-215 O-2-F—Ph H H 4-OCH₂CF₃  82-83 3-216 O—s-Bu H H4-OCH₂CF₂CF₂H 1.4905 (28.5) 3-217 O—s-Bu H H 4-O—i-Pr 1.3353 (22.2)3-218 O—s-Bu H H 3-F-4-O—i-Pr 1.4028 (22.2) 3-219 OMe H H 4-n-Pr  39-403-220 OMe H H 4-c-Pr 3-221 O—n-Pr H H 4-c-Pr 3-222 O—i-Pr H H 4-c-Pr3-223 O—i-Bu H H 4-c-Pr  38-39 3-224 O—s-Bu H H 4-c-Pr 1.5249 (21.3)3-225 O-2-F—Ph H H 4-c-Pr 1.5842 (19.7) 3-226 OMe H H 4-OMe 3-227 O—n-PrH H 4-OMe 3-228 O—i-Pr H H 4-OMe 3-229 O—i-Bu H H 4-OMe 1.5434 (21.3)3-230 O—s-Bu H H 4-OMe 1.5413 (21.3) 3-231 OMe H H 4-CH₂OCH₂CF₃ 3-232O—n-Pr H H 4-CH₂OCH₂CF₃ 3-233 O—i-Pr H H 4-CH₂OCH₂CF₃ 3-234 O—i-Bu H H4-CH₂OCH₂CF₃ 3-235 O—s-Bu H H 4-CH₂OCH₂CF₃ 1.4422 (21.3) 3-236 SOMe H H4-t-Bu 3-237 SO₂Me H H 4-t-Bu 3-238 SOEt H H 4-t-Bu 3-239 SO₂Et H H4-t-Bu 3-240 S—i-Pr H H 4-t-Bu 3-241 SO—i-Pr H H 4-t-Bu 3-242 SO₂—i-Pr HH 4-t-Bu 3-243 SPh H H 4-t-Bu 1.5906 (22.2) 3-244 SOPh H H 4-t-Bu 3-245SO₂Ph H H 4-t-Bu 3-246 SOMe H H 4-CF₃ 3-247 SO₂Me H H 4-CF₃ 3-248 SOEt HH 4-CF₃ 3-249 SO₂Et H H 4-CF₃ 3-250 S—i-Pr H H 4-CF₃ 3-251 SO—i-Pr H H4-CF₃ 3-252 SO₂—i-Pr H H 4-CF₃ 3-253 SPh H H 4-CF₃  67-68 3-254 SOPh H H4-CF₃ 149-150 3-255 SO₂Ph H H 4-CF₃ 129-130 3-256 SMe H H 4-OCF₃ 3-257SOMe H H 4-OCF₃ 3-258 SO₂Me H H 4-OCF₃ 3-259 SEt H H 4-OCF₃ 3-260 SOEt HH 4-OCF₃ 3-261 SO₂Et H H 4-OCF₃ 3-262 S—i-Pr H H 4-OCF₃ 3-263 SO—i-Pr HH 4-OCF₃ 3-264 SO₂—i-Pr H H 4-OCF₃ 3-265 SPh H H 4-OCF₃  42-43 3-266SOPh H H 4-OCF₃ 3-267 SO₂Ph H H 4-OCF₃ 3-268 O-3-Py H H 4-CF₃ 3-269O-4-Py H H 4-CF₃

TABLE 4 com- prop- pound erty No. AR¹ R² R³ (X)_(m) value remarks 4-1OMe H H 4-t-Bu hydrochloride 4-2 OMe H H 4-t-Bu paratosylate 4-3 OMe H H4-t-Bu oxalate 4-4 O-n-Pr H H 4-t-Bu hydrochloride 4-5 O-n-Pr H H 4-t-Buparatosylate 4-6 O-n-Pr H H 4-t-Bu oxalate 4-7 O-i-Pr H H 4-t-Buhydrochloride 4-8 O-i-Pr H H 4-t-Bu paratosylate 4-9 O-i-Pr H H 4-t-Buoxalate  4-10 O-i-Bu H H 4-t-Bu 120-128 hydrochloride  4-11 O-i-Bu H H4-t-Bu 119-121 paratosylate  4-12 O-i-Bu H H 4-t-Bu 137-141 oxalate 4-13 O-s-Bu H H 4-t-Bu hydrochloride  4-14 O-s-Bu H H 4-t-Buparatosylate  4-15 O-s-Bu H H 4-t-Bu oxalate  4-16 OPh H H 4-t-Buhydrochloride  4-17 OPh H H 4-t-Bu paratosylate  4-18 OPh H H 4-t-Buoxalate  4-19 O-2-F—Ph H H 4-t-Bu hydrochloride  4-20 O-2-F—Ph H H4-t-Bu paratosylate  4-21 O-2-F—Ph H H 4-t-Bu oxalate  4-22 OMe H H4-TMS hydrochloride  4-23 OMe H H 4-TMS paratosylate  4-24 OMe H H 4-TMSoxalate  4-25 O-n-Pr H H 4-TMS hydrochloride  4-26 O-n-Pr H H 4-TMSparatosylate  4-27 O-n-Pr H H 4-TMS oxalate  4-28 O-i-Pr H H 4-TMShydrochloride  4-29 O-i-Pr H H 4-TMS paratosylate  4-30 O-i-Pr H H 4-TMSoxalate  4-31 O-i-Bu H H 4-TMS hydrochloride  4-32 O-i-Bu H H 4-TMSparatosylate  4-33 O-i-Bu H H 4-TMS oxalate  4-34 O-s-Bu H H 4-TMShydrochloride  4-35 O-s-Bu H H 4-TMS paratosylate  4-36 O-s-Bu H H 4-TMSoxalate  4-37 OPh H H 4-TMS hydrochloride  4-38 OPh H H 4-TMSparatosylate  4-39 OPh H H 4-TMS oxalate  4-40 O-2-F—Ph H H 4-TMShydrochloride  4-41 O-2-F—Ph H H 4-TMS paratosylate  4-42 O-2-F—Ph H H4-TMS oxalate  4-43 OMe H H 4-CF₃ hydrochloride  4-44 OMe H H 4-CF₃paratosylate  4-45 OMe H H 4-CF₃ oxalate  4-46 O-n-Pr H H 4-CF₃hydrochloride  4-47 O-n-Pr H H 4-CF₃ paratosylate  4-48 O-n-Pr H H 4-CF₃oxalate  4-49 O-i-Pr H H 4-CF₃ hydrochloride  4-50 O-i-Pr H H 4-CF₃paratosylate  4-51 O-i-Pr H H 4-CF₃ oxalate  4-52 O-i-Bu H H 4-CF₃hydrochloride  4-53 O-i-Bu H H 4-CF₃ paratosylate  4-54 O-i-Bu H H 4-CF₃oxalate  4-55 O-s-Bu H H 4-CF₃ 110-115 hydrochloride  4-56 O-s-Bu H H4-CF₃ 97-99 paratosylate  4-57 O-s-Bu H H 4-CF₃ 115-119 oxalate  4-58OPh H H 4-CF₃ hydrochloride  4-59 OPh H H 4-CF₃ paratosylate  4-60 OPh HH 4-CF₃ oxalate  4-61 O-2-F—Ph H H 4-CF₃ hydrochloride  4-62 O-2-F—Ph HH 4-CF₃ paratosylate  4-63 O-2-F—Ph H H 4-CF₃ oxalate  4-64 OMe H H2-F-4-CF₃ hydrochloride  4-65 OMe H H 2-F-4-CF₃ paratosylate  4-66 OMe HH 2-F-4-CF₃ oxalate  4-67 O-n-Pr H H 2-F-4-CF₃ hydrochloride  4-68O-n-Pr H H 2-F-4-CF₃ paratosylate  4-69 O-n-Pr H H 2-F-4-CF₃ oxalate 4-70 O-i-Pr H H 2-F-4-CF₃ hydrochloride  4-71 O-i-Pr H H 2-F-4-CF₃paratosylate  4-72 O-i-Pr H H 2-F-4-CF₃ oxalate  4-73 O-i-Bu H H2-F-4-CF₃ hydrochloride  4-74 O-i-Bu H H 2-F-4-CF₃ paratosylate  4-75O-i-Bu H H 2-F-4-CF₃ oxalate  4-76 O-s-Bu H H 2-F-4-CF₃ hydrochloride 4-77 O-s-Bu H H 2-F-4-CF₃ paratosylate  4-78 O-s-Bu H H 2-F-4-CF₃oxalate  4-79 OPh H H 2-F-4-CF₃ hydrochloride  4-80 OPh H H 2-F-4-CF₃paratosylate  4-81 OPh H H 2-F-4-CF₃ oxalate  4-82 OMe H H 4-OCF₃hydrochloride  4-83 OMe H H 4-OCF₃ paratosylate  4-84 OMe H H 4-OCF₃oxalate  4-85 O-n-Pr H H 4-OCF₃ hydrochloride  4-86 O-n-Pr H H 4-OCF₃paratosylate  4-87 O-n-Pr H H 4-OCF₃ oxalate  4-88 O-i-Pr H H 4-OCF₃hydrochloride  4-89 O-i-Pr H H 4-OCF₃ paratosylate  4-90 O-i-Pr H H4-OCF₃ oxalate  4-91 O-i-Bu H H 4-OCF₃ hydrochloride  4-92 O-i-Bu H H4-OCF₃ paratosylate  4-93 O-i-Bu H H 4-OCF₃ oxalate  4-94 O-s-Bu H H4-OCF₃ hydrochloride  4-95 O-s-Bu H H 4-OCF₃ paratosylate  4-96 O-s-Bu HH 4-OCF₃ oxalate  4-97 OPh H H 4-OCF₃ hydrochloride  4-98 OPh H H 4-OCF₃paratosylate  4-99 OPh H H 4-OCF₃ oxalate  4-100 OMe H H 4-OCF₃hydrochloride  4-101 OMe H H 4-OCF₃ paratosylate  4-102 OMe H H 4-OCF₃oxalate  4-103 O-n-Pr H H 4-OCF₃ hydrochloride  4-104 O-n-Pr H H 4-OCF₃paratosylate  4-105 O-n-Pr H H 4-OCF₃ oxalate  4-106 O-i-Bu H H 4-OCF₃hydrochloride  4-107 O-i-Bu H H 4-OCF₃ paratosylate  4-108 O-i-Bu H H4-OCF₃ oxalate  4-109 O-s-Bu H H 4-OCF₃ hydrochloride  4-110 O-s-Bu H H4-OCF₃ paratosylate  4-111 O-s-Bu H H 4-OCF₃ oxalate  4-112 OPh H H4-OCF₃ hydrochloride  4-113 OPh H H 4-OCF₃ paratosylate  4-114 OPh H H4-OCF₃ oxalate  4-115 OMe H H 4-i-Pr hydrochloride  4-116 OMe H H 4-i-Prparatosylate  4-117 OMe H H 4-i-Pr oxalate  4-118 O-n-Pr H H 4-i-Prhydrochloride  4-119 O-n-Pr H H 4-i-Pr paratosylate  4-120 O-n-Pr H H4-i-Pr oxalate  4-121 O-i-Pr H H 4-i-Pr hydrochloride  4-122 O-i-Pr H H4-i-Pr paratosylate  4-123 O-i-Pr H H 4-i-Pr oxalate  4-124 O-i-Bu H H4-i-Pr hydrochloride  4-125 O-i-Bu H H 4-i-Pr paratosylate  4-126 O-i-BuH H 4-i-Pr oxalate  4-127 O-s-Bu H H 4-i-Pr hydrochloride  4-128 O-s-BuH H 4-i-Pr paratosylate  4-129 O-s-Bu H H 4-i-Pr oxalate  4-130 OPh H H4-i-Pr hydrochloride  4-131 OPh H H 4-i-Pr paratosylate  4-132 OPh H H4-i-Pr oxalate  4-133 OMe H H 4-i-Bu hydrochloride  4-134 OMe H H 4-i-Buparatosylate  4-135 OMe H H 4-i-Bu oxalate  4-136 O-n-Pr H H 4-i-Buhydrochloride  4-137 O-n-Pr H H 4-i-Bu paratosylate  4-138 O-n-Pr H H4-i-Bu oxalate  4-139 O-i-Pr H H 4-i-Bu hydrochloride  4-140 O-i-Pr H H4-i-Bu paratosylate  4-141 O-i-Pr H H 4-i-Bu oxalate  4-142 O-i-Bu H H4-i-Bu hydrochloride  4-143 O-i-Bu H H 4-i-Bu paratosylate  4-144 O-i-BuH H 4-i-Bu oxalate  4-145 O-s-Bu H H 4-i-Bu hydrochloride  4-146 O-s-BuH H 4-i-Bu paratosylate  4-147 O-s-Bu H H 4-i-Bu oxalate  4-148 OPh H H4-i-Bu hydrochloride  4-149 OPh H H 4-i-Bu paratosylate  4-150 OPh H H4-i-Bu oxalate  4-151 OMe H H 4-F hydrochloride  4-152 OMe H H 4-Fparatosylate  4-153 OMe H H 4-F oxalate  4-154 O-n-Pr H H 4-Fhydrochloride  4-155 O-n-Pr H H 4-F paratosylate  4-156 O-n-Pr H H 4-Foxalate  4-157 O-i-Pr H H 4-F hydrochloride  4-158 O-i-Pr H H 4-Fparatosylate  4-159 O-i-Pr H H 4-F oxalate  4-160 O-i-Bu H H 4-Fhydrochloride  4-161 O-i-Bu H H 4-F paratosylate  4-162 O-i-Bu H H 4-Foxalate  4-163 O-s-Bu H H 4-F hydrochloride  4-164 O-s-Bu H H 4-Fparatosylate  4-165 O-s-Bu H H 4-F oxalate  4-166 OPh H H 4-Fhydrochloride  4-167 OPh H H 4-F paratosylate  4-168 OPh H H 4-F oxalate 4-169 OMe H H 4-Cl hydrochloride  4-170 OMe H H 4-Cl paratosylate 4-171 OMe H H 4-Cl oxalate  4-172 O-n-Pr H H 4-Cl hydrochloride  4-173O-n-Pr H H 4-Cl paratosylate  4-174 O-n-Pr H H 4-Cl oxalate  4-175O-i-Pr H H 4-Cl hydrochloride  4-176 O-i-Pr H H 4-Cl paratosylate  4-177O-i-Pr H H 4-Cl oxalate  4-178 O-i-Bu H H 4-Cl hydrochloride  4-179O-i-Bu H H 4-Cl paratosylate  4-180 O-i-Bu H H 4-Cl oxalate  4-181O-s-Bu H H 4-Cl hydrochloride  4-182 O-s-Bu H H 4-Cl paratosylate  4-183O-s-Bu H H 4-Cl oxalate  4-184 OPh H H 4-Cl hydrochloride  4-185 OPh H H4-Cl paratosylate  4-186 OPh H H 4-Cl oxalate  4-187 OMe H H Hhydrochloride  4-188 OMe H H H paratosylate  4-189 OMe H H H oxalate 4-190 O-n-Pr H H H hydrochloride  4-191 O-n-Pr H H H paratosylate 4-192 O-n-Pr H H H oxalate  4-193 O-i-Pr H H H hydrochloride  4-194O-i-Pr H H H paratosylate  4-195 O-i-Pr H H H oxalate  4-196 O-i-Bu H HH hydrochloride  4-197 O-i-Bu H H H paratosylate  4-198 O-i-Bu H H Hoxalate  4-199 O-s-Bu H H H hydrochloride  4-200 O-s-Bu H H Hparatosylate  4-201 O-s-Bu H H H oxalate  4-202 OPh H H H hydrochloride 4-203 OPh H H H paratosylate  4-204 OPh H H H oxalate

TABLE 5 NMR data compound No. ¹H-NMR(CDCl₃/TMS, ppm) 3-4 8.39(1H, s),8.07(1H, s), 7.39(4H, s), 5.47(2H, s), 4.13(1H, m), 1.68(4H, m),1.32(9H, s), 0.95(6H, t)

The agrohorticultural insecticides containing the benzyloxypyrimidinederivative represented by the formula (I) of the present invention as anactive ingredient are suitable for controlling various insect pests suchas agrohorticultural insect pests, stored grain insect pests, sanitaryinsect pests, nematodes, etc., which are injurious to paddy rice, fruittrees, vegetables, other crops, flowers and ornamental plants, etc. Theyhave a marked insecticidal effect, for example, on Lepidoptera includingsummer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix(Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), orientalfruit moth (Grapholita molesta), soybean pod borer (Leguminivoraglycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller(Caloptilia thevivora), Caloptilia sp. (Caloptilia zachrysa), appleleafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrinaastaurota), common white (Pieris rapae crucivora), tobacco budworm(Helicoverpa sp.), codling moth (Laspey resia pomonella), diamondbackmoth (Plutella xylostella), apple fruit moth (Argyresthia conjugella),peach fruit moth (Carposina niponensis), rice stem borer (Chilosuppressalis), rice leafroller (Cnaphalocrocis medinalis), tobacco moth(Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), yellow riceborer (Scirpophaga incertulas), rice skipper (Parnara guttata), ricearmyworm (Pseudaletia separata), pink borer (Sesamia inferens), commoncutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), etc.;Hemiptera including aster leafhopper (Macrosteles fascifrons), greenrice leafhopper (Nephotettix cincticeps), brown rice planthopper(Nilaparvata lugens), whitebacked rice planthopper (Sogatellafurcifera), citrus psylla (Diaphorina citri), grape whitefly(Aleurolobus taonabae), sweetpotato whitefly (Bemisia tabaci),greenhouse whitefly (Trialeurodes vaporariorum), turnip aphid (Lipaphiserysimi), green peach aphid (Myzus persicae), Indian wax scale(Ceroplastes ceriferus), cottony citrus scale (Chloropulvinariaaurantii), camphor scale (Pseudaonidia duplex), san Jose scale(Comstockaspis perniciosa), arrowhead scale (Unaspis yanonensis), etc.;Coleoptera including meadow nematode (Pratylenchus sp.), soybean beetle(Anomala rufocuprea), Japanese beetle (Popillia japonica), tobaccobeetle (Lasioderma serricorne), powderpost beetle (Lyctus brunneus),twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), azukibean weevil (Callosobruchus chinensis), vegetable weevil (Listroderescostirostris), maize weevil (Sitophilus zeamais), boll weevil(Anthonomus grandis), rice water weevil (Lissorhoptrus oryzophilus),cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulemaoryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle(Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata),Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabroticasp.), etc.;

-   Diptera including melon fly (Dacus cucurbitae), oriental fruit fly    (Bactrocera dorsalis), rice leafminer (Agromyza oryzae), onion    maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod    gall midge (Asphondylia sp.), house fly (Musca domestica), common    house mosquito (Culex pipiens pallens), etc.;-   Tylenchida including root-lesion nematode (Pratylenchus sp.), potato    cyst nematode (Globodera rostochiensis), root-knot nematode    (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans),    Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar nematode    (Aphelenchoides ritzemabosi), etc.; and-   Acarina including citrus red mite (Panonychus citri), fruit tree red    spider mite (Panonychus ulmi), carmine spider mite (Tetranychus    cinnabarinus), Kanzawa spider mite (Tetranychus Kanzawai Kishida),    two-spotted spider mite (Tetranychus urticae Koch), pink tea rust    mite (Acaphylla theae), pink citrus rust mite (Aculops pelekassi),    purple tea mice (Calacarus carinatus), pear rust mite (Epitrimerus    pyri), etc.

In addition, it shows a remarkable termiticidal effect with a low doseagainst any termites including Rhinotermitidae such as formosansubterranean termite (Coptotermes formosanus Shiraki), Japanesesubterranean termite (Reticulitermes speratus (Kolbe)); Reticulitermeshesperus, Reticulitermes tibialis, Reticulitermes flavipes etc.occurring in North America; Reticulitermes lucifugus, Reticulitermessantonensis etc. occurring on the coast of the Mediterranean Sea,America common dry-wood termite (Incisitermes minor (Hagen)); Termitidaesuch as Formosan termite (Odontotermes formosanus (Shiraki)),Kalotermitidae such as Daikoku dry-wood termite (Cryptotermes domesticus(Haviland)) and Termopsidae such as Hodotermopsis japonica (Holmgren)and the like, that damage house, architectural materials, furniture,leather, fiber, plastic processing product, electric cable, cables andthe like. Moreover, it also shows a remarkable formicidal effect with alow dose against ants including Formicidae such as little black ant(Monomorium pharaonis Linnes), Monomorium nipponense Wheeler, Camponotuskiusiuensis Santschi, negro ant (Formica japonica Motschulsky), Lasiusfuliginosus (Latreille) and the like, fire ant (Solenopsis richteri,Solenopsis invicta, Solenopsis geminata(F)) and the like occurring inNorth America, that invade agricultural crops, public facility in parksand the like, and houses and harm people.

Furthermore, the benzyloxypyrimidine derivative represented by theformula (I) of the present invention can also be used againstectoparasite in domestic animals such as cattle, horse, sheep and thelike, pets such as dog, cat and the like, Simplicidentata animals suchas mouse, rat, hamster, squirrel and the like, Carnivora animals such asLagomorpha animal, ferret and the like, and birds such as duck, chicken,dove and the like and has a strong insecticidal effect againstectoparasites, for example, Aphaniptera pests such as cat flea(Ctenocephalides felis), dog flea (Ctenocephalides canis), Xenopsyllacheopis and the like, Acari pests such as Haemaphysalis longicornis,Boophilus microplus and the like, Anoplura pests such as cattle louse(Haematopinus eurysternus), Damalinia ovis and the like.

The agrohorticultural insecticide containing the benzyloxypyrimidinederivative represented by the formula (I) of the present invention as anactive ingredient has a marked controlling effect on theabove-exemplified insect pests, which are injurious to paddy fieldcrops, upland crops, fruit trees, vegetables and other crops, flowersand ornament plants, and the like. Therefore, the desired effect of theagrohorticultural insecticides of the present invention can be exhibitedby applying the agents to the cultivation carrier such as seeds, paddyfield water, stalks and leaves or soil of propagation facility, paddyfield, field, fruit trees, vegetables, other crops or flowers andornament plants and the like, at a season at which the insect pests areexpected to appear, before their appearance or at the time when theirappearance is confirmed. Particularly, preferable use form isapplication utilizing what is called penetration transferability byallowing absorption of the compound of the present invention from rootsvia or not via soil, by treating propagation soil for crops, flowers andornamental plants and the like, planting hole soil for transplantation,plant foot, irrigation water, culture water for hydroponic culture andthe like.

Recently, gene recombinant crop (herbicide resistant crop, insect pestresistant crop incorporated with insecticidal toxin generating gene,disease resistant crop incorporated with disease resistance inducerproducing gene, taste improved crop, preservability improved crop, yieldimproved crop, etc.), insect sex pheromone (pheromone disruptingchemicals for leaf roller moths, cabbage armyworm, etc.), IPM(integrated pest management) technology using natural enemy insect havebeen progressed, and the agrohorticultural insecticide of the presentinvention can be used in combination with or by systematization withsuch technologies.

The plants, for which the agrohorticultural insecticide of the presentinvention can be used, are not specifically limited and, for example, itcan be used for the following plants.

It can be applied to plants such as cereals (e.g. rice, barley, wheat,rye, oat, corn etc.); legume (soybean, adzuki bean, fava bean, bean,kidney bean, peanut, etc.); fruit trees and fruits (apple, citrusfruits, pear, grapes, peach, plum, cherry fruit, walnut, sweet chestnut,almond, banana, strawberry, etc.); vegetables (cabbage, tomato, spinach,broccoli, lettuce, onion, welsh onion, green pepper, eggplant, pepperetc.); root vegetables (carrot, potato, sweet potato, tannia, radish,lotus root, turnip, burdock, garlic etc.); crop for processing (cotton,hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco,tea, etc.); gourd (pumpkin, cucumber, oriental melon, watermelon, melon,etc.); feed crop (orchard grass, sorghum, timothy, clover, alfalfa,etc.); grass (Korean lawn grass, bent grass, etc.); crop for spicery(lavender, rosemary, thyme, parsley, pepper, ginger, etc.); flowers(chrysanthemum, rose, carnation, orchid, etc.), garden tree (gingko,Japanese cherry, aucuba etc.), forest tree (Abies sachalinensis, Piceajezoensis, pines, Thujopsis dolabrata, Japanese cedar, Japanese cypressetc.) and the like.

For control of various pests, the agrohorticultural insecticide of thepresent invention need only be applied to the plant expected to allowdevelopment of pests and nematode, as it is or after being properlydiluted with or suspended in water or the like, in an amount effectivefor control of the pests or nematode. For example, for pests andnematodes that occur in fruit trees, cereals, vegetables and the like,the insecticide is sprayed on the stem and leaf parts, or absorbed fromthe root by seed treatments such as dipping the seeds in a drug,dressing of seeds, Calper treatment and the like, soil treatment such assoil whole layer blending, planting row application, bed soil blending,cell seedling treatment, planting hole treatment, plant foot treatment,top dress, box treatment of rice, water surface application etc., andthe like. In addition, the agrohorticultural insecticide can also beused by application to a culture fluid for culture fluid (hydroponic)culture, application by smoking or tree stem injection and the like.

The agrohorticultural insecticide of the present invention need only beapplied to the place expected to allow development of pests, as it is orafter being properly diluted with or suspended in water or the like, inan amount effective for control of the pests. For example, spraying ongrain-storage insects, house pests, hygiene pests, forest pests and thelike, as well as application, smoking, bait to house and architecturalmaterials and the like can also be employed for use.

As methods for seed treatment, conventional methods such as a methodcomprising penetration of the agent by dipping of seeds in the liquidagent obtained by diluting or not a liquid formulation or a solidformulation, a method comprising adhering a solid formulation or liquidformulation to the seed surface by admixing the formulation with seeds,dressing and the like, a method comprising admixing the formulation withadhesive carriers such as resin, polymer and the like and forming a coaton the seeds, a method comprising application near the seedssimultaneously with planting and the like can be mentioned.

The “seed” to be subjected to the seed treatment means a plant body inan early stage of growth, which is used for propagation, and includesseeds, as well as bulb, tuber, seed potato, germ, propagule, scaly bulb,a plant body for vegetative propagation by cutting propagation, and thelike.

The “soil” and “cultivation carrier” for plant when practicing themethod of use of the present invention mean supports for cultivation ofplants, particularly supports for growing roots, and the material is notparticularly limited. The material may be any as long as plants can growtherein and specific materials include, for example, soils, nursery mat,water and the like. As a specific material, sand, pumice, vermiculite,diatomaceous earth, agar, gelled substance, polymer substance, rockwool, glass wool, wood chip, bark and the like can also be used.

As a method of application to crop plant stem and leaves, orgrain-storage insect, house pest, hygiene pest or forest pest, a methodincluding appropriately diluting a liquid formulation such as emulsion,flowable formulation and the like or a solid formulation such as awettable powder or water dispersible granule and the like with water andspraying same, a method of spraying a dust, or smoking and the like canbe mentioned.

For application to the soil, for example, a method comprisingapplication of a liquid formulation to the plant foot of plant body,nursery for raising seedling and the like with or without dilution inwater, a method comprising application of granules to the plant foot ofplant body or nursery for raising seedling, a method comprisingapplication of dust, wettable powder, water dispersible granule, granuleand the like before sowing or transplantation to allow them to beincorporated into the entire soil, a method comprising applicationplanting pit, planting row and the like with dust, wettable powder,water dispersible granule, granule and the like before sowing orplanting and the like can be mentioned.

In the case of the paddy rice nursery box, the formulation may varydepending on the timing of, for example, application on sowing,application during greening, application during transplanting and thelike. The formulations of dust, water dispersible granule, granule andthe like can be employed. Application is also possible by incorporationinto the grove soil, wherein the grove soil may be mixed with dust,water dispersible granule, granule and the like and, for example,incorporation into bed soil, incorporation into cover soil,incorporation into the entire grove soil and the like can be employed.Simply, a grove soil and various formulations may be applied inalternate layers.

As a method of application to a paddy field, a solid formulation such asjumbo, pack, granule, water dispersible granule and the like, a liquidformulation such as flowable, emulsion and the like are generallysprayed on a flooded paddy field. Alternatively, during rice planting, asuitable formulation can also be applied or injected to soil directly orafter blending with a fertilizer. Moreover, by utilizing a liquid agentsuch as emulsion, flowable and the like to a is water inlet and the flowsource of water into paddy fields such as an irrigation apparatus andthe like, a saving application along with the supply of water can alsobe performed.

For upland crops, treatment of seeds, a cultivation carrier to be placednear the plant body and the like during the period of from sowing toraising seedling is possible. For plants to be directly sown in thefield, a direct treatment of seeds, a treatment of a plant foot of theplant under cultivation and the like are preferable. An application ofgranules, a soil injection treatment with a liquid agent with or withoutdilution with water and the like can be performed. It is also apreferable treatment to blend granules with a cultivation carrier beforeseeding, and seed the blend.

For a treatment on sowing or during raising seedling of a cultivatedplant to be transplanted, a direct treatment of seeds, an soil injectiontreatment of nursery for raising seedling with a liquid agent or adispersal treatment thereof with granules are preferable. In addition,treatment of a planting pit with granules and mixing of a cultivationcarrier to be placed near the transplantation site with the granulesduring fix planting are also preferable treatments.

The agrohorticultural insecticide of the present invention is generallyprepared into conveniently usable forms according to an ordinary mannerfor preparation of agrochemicals.

That is, the benzyloxypyrimidine derivative represented by the formula(I) of the present invention are blended with a suitable inert carrierand, optionally, an adjuvant in a proper proportion and prepared into asuitable preparation form such as a suspension, emulsifiableconcentrate, soluble concentrate, wettable powder, granular wettablepowder, granules, dust, tablets, pack or the like through dissolution,dispersion, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier usable in the present invention may be either solid orliquid. As a material usable as the solid carrier, there can beexemplified soybean flour, cereal flour, wood flour, bark flour, sawdust, powdered tobacco stalks, powdered walnut shells, bran, powderedcellulose, extraction residue of vegetables, resins such as powderedsynthetic polymers and the like, clays (e.g. kaolin, bentonite, and acidclay), talcs (e.g. talc and pyrophyllite), silica powders or flakes(e.g. diatomaceous earth, silica sand, mica and white carbon [synthetic,high-dispersion silicic acid, also called finely divided hydrated silicaor hydrated silicic acid, some of commercially available productscontain calcium silicate as the major component]), inorganic or mineralpowders such as activated carbon, powdered sulfur, pumice, calcineddiatomaceous earth, ground brick, fly ash, sand, calcium carbonate,calcium phosphate and the like, plastic carriers such as polyethylene,polypropylene, poly(vinylidene chloride) and the like, chemicalfertilizers (e.g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, urea and ammonium chloride), and compost. These carriers may beused alone or as a mixture of two or more kinds thereof.

A material usable as the liquid carrier is selected from materials thathave solubility in themselves or which, even without such solubility,are capable of dispersing an active ingredient with the aid of anadjuvant. The following are typical examples of the liquid carrier andcan be used alone or as a mixture of two or more kinds thereof: water,alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethyleneglycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutylketone, diisobutyl ketone and cyclohexanone), ethers (e.g. ethyl ether,dioxane, cellosolve, dipropyl ether and tetrahydrofuran), aliphatichydrocarbons (e.g. kerosene and mineral oils), aromatic hydrocarbons(e.g. benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes),halogenated hydrocarbons (e.g. dichloroethane, chloroform, carbontetrachloride and chlorobenzene), esters (e.g. ethyl acetate,diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), amides(e.g. dimethylformamide, diethylformamide and dimethylacetamide),nitriles (e.g. acetonitrile), and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are useddepending upon purposes and used alone or in combination of two or morekinds, or in some cases, need not be used at all.

To emulsify, disperse, dissolve and/or wet a compound as an activeingredient, a surfactant such as polyoxyethylene alkyl ethers,polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acidesters, polyoxyethylene resonates, polyoxyethylene sorbitan monolaurate,polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates and higher alcoholsulfate esters can be used.

Further, to stabilize dispersion of, tackify and/or bind the compound asan active ingredient, casein, gelatin, starch, methyl cellulose,carboxymethyl cellulose, gum arabic, poly(vinyl alcohol)s, turpentine,bran oil, bentonite and ligninsulfonates and the like can be used. Toimprove the flowability of a solid product, waxes, stearates, alkylphosphates and the like can be used.

Adjuvants such as naphthalenesulfonic acid condensation products andpolycondensates of phosphates may be used as a peptizer for dispersibleproducts, silicone oil and the like may also be used as a defoamingagent, and 1,2-benzisothiazolin-3-one, p-chloro-m-xylenol, butylp-hydroxybenzoate and the like may also be used as a preservative.

Further, if necessary, functional spreading agents, active enhancerssuch as metabolic decomposition inhibitor like piperonyl butoxide,anti-freezing agents such as propylene glycol, antioxidizing agents suchas BHT, ultraviolet absorbers, and other aids may also be used.

The content of the compound as active ingredient may be varied asrequired, and the compound as active ingredient may be used in aproportion properly chosen in the range of 0.01 to 90 parts by weightper 100 parts of the agrohorticultural agents of the present invention.For example, in dusts, granules, emulsion or wettable powders, thesuitable content of the compound as active ingredient is from 0.01 to50% by weight.

The applying dosage of the agrohorticultural insecticide of the presentinvention varies depending upon various factors such as a purpose,insect pests to be controlled, a growth state of a plant, tendency ofinsect pests appearance, weather, environmental conditions, apreparation form, an application method, an application site andapplication time. It may be properly chosen in the range of 0.001 g to10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as activeingredient) per 10 ares depending upon purposes.

The agrohorticultural insecticide of the present invention may be usedin admixture with other agrohorticultural insecticides, acaricides,nematocides, fungicides, biotic pesticides or the like in order toexpand both spectrum of controllable disease and insect pest and theperiod of time when effective application are possible or to reduce thedosage. Furthermore, the agrohorticultural insecticide of the presentinvention may be used in admixture with herbicides, plant growthregulators, fertilizers or the like, depending upon applicationsituations.

As the other agrohorticultural insecticides, acaricides and nematocides,which are used for the above purpose, there can be exemplifiedagrohorticultural insecticides, acaricides and nematocides, such asEthion, Trichlorfon, Methamidophos, Acephate, Dichlorvos, Mevinphos,Monocrotophos, Malathion, Dimethoate, Formothion, Mecarbam, Vamidothion,Thiometon, Disulfoton, Oxydeprofos, Naled, Methyl parathion,Fenitrothion, Cyanophos, Propaphos, Fenthion, Prothiofos, Profenofos,Isofenphos, Temephos, Phenthoate, Dimethylvinphos, Chlorfenvinphos,Tetrachlorvinphos, Phoxim, Isoxathion, Pyraclofos, Methidathion,Chlorpyrifos, Chlorpyrifos-methyl, Pyridaphenthion, Diazinon,Pirimiphos-methyl, Phosalone, Phosmet, Dioxabenzofos, Quinalphos,Terbufos, Ethoprophos, Cadusafos, Mesulfenfos, DPS (NK-0795),Phosphocarb, Fenamiphos, Isamidofos, Fosthiazate, Isazofos, Ethoprophos,Fenthion, Fostietane, Dichlofenthion, Thionazin, Sulprofos,Fensulfothion, Diamidafos, Pyrethrin, Allethrin, Prallethrin,Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropathrin,Cypermethrin, α-Cypermethrin, Cyhalothrin, λ-Cyhalothrin, Deltamethrin,Acrinathrin, Fenvalerate, Esfenvalerate, Cycloprothrin, Etofenprox,Halfenprox, Silafluofen, Flucythrinate, Fluvalinate, Methomyl, Oxamyl,Thiodicarb, Aldicarb, Alanycarb, Cartap, Metolcarb, Xylylcarb, Propoxur,Fenoxycarb, fenobucarb, Ethiophencarb, Fenothiocarb, Bifenazate,Carbaryl, Pirimicarb, Carbofuran, Carbosulfan, Furathiocarb,Benfuracarb, Aldoxycarb, Diafenthiuron, Diflubenzuron, Teflubenzuron,Hexaflumuron, Novaluron, Lufenuron, Flufenoxuron, Chlorfluazuron,Fenbutatin oxide, Tricyclohexyltin hydroxide, Sodium oleate, Potassiumoleate, Methoprene, Hydroprene, Binapacryl, Amitraz, Dicofol, Kelthane,Chlorobenzilate, Phenisobromolate, Tetradifon, Bensultap, Benzoximate,Tebufenozide, Methoxyfenozide, Pyridalyl, Flubendiamide,Pyrifluquinazon, metaflumizone, chlorantraniliprole, cyantraniliprole,Chromafenozide, Propargite, Acequinocyl, Endosulfan, Diofenolan,Chlorfenapyr, Fenpyroximate, Tolfenpyrad, Fipronil, Tebufenpyrad,Triazamate, Etoxazole, Hexythiazox, Nicotine sulfate, Nitenpyram,Acetamiprid, Thiacloprid, Imidacloprid, Thiamethoxam, Clothianidin,Dinotefuran, Fluazinam, Pyriproxyfen, Hydramethylnon, Pyrimidifen,Pyridaben, Cyromazine, TPIC (tripropyl isocyanurate), Pymetrozine,Clofentezine, Buprofezin, Thiocyclam, Fenazaquin, Chinomethionate,Indoxacarb, Polynactin complexes, Milbemectin, Abamectin,Emamectin-benzoate, Spinosad, BT (Bacillus thuringiensis), Azadirachtin,Rotenone, Hydroxypropyl starch, Levamisole hydrochloride, Metam-sodium,Morantel tartrate, Dazomet, Trichlamide, Pasteuria penetrans,Monacrosporium-phymatophagum, etc.

As the agrohorticultural fungicides used for the same purpose as above,there can be exemplified agrohorticultural fungicides such as Sulfur,Lime sulfur, Copper sulfate basic, Iprobenfos, Edifenphos,Tolclofos-methyl, Thiram, Polycarbamate, Zineb, Maneb, Mancozeb,Propineb, Thiophanate, Thiophanate methyl, Benomyl, Iminoctadineacetate, Iminocutadine albecylate, Mepronil, Flutolanil, Pencycuron,Furametpyr, Thifluzamide, Metalaxyl, Oxadixyl, Carpropamid,Dichlofluanid, Flusulfamide, Chlorothalonil, Kresoxim-methyl, Fenoxanil,Hymexazol, Etridiazole, Fluoroimide, Procymidone, Vinclozolin,Iprodione, Triadimefon, Triflumizole, Bitertanol, Ipconazole,Fluconazole, Propiconazole, Difenoconazole, Myclobutanil, Tetraconazole,Hexaconazole, Tebuconazole, Imibenconazole, Prochloraz, Pefurazoate,Cyproconazole, Isoprothiolane, Fenarimol, Pyrimethanil, Mepanipyrim,Pyrifenox, Fluazinam, Triforine, Diclomezine, Azoxystrobin,trifloxystrobin, orysastrobin, Thiadiazine, Captan, Probenazole,Acibenzolar-S-methyl(CGA-245704), Fthalide, Tricyclazole, Pyroquilon,Chinomethionat, Oxolinic acid, Dithianon, cyazofamid, Diclocymet,Kasugamycin, Validamycin, Polyoxin, Blasticidin, Streptomycin, Isotianiletc.

Similarly, as the herbicides, there can be exemplified herbicides suchas Glyphosate, Sulfosate, Glufosinate, Bialaphos, Butamifos, Esprocarb,Prosulfocarb, Benthiocarb, Pyributicarb, Asulam, Linuron, Dymron,Isouron, Bensulfuron methyl, Cyclosulfamuron, Cinosulfuron,Pyrazosulfuron ethyl, Azimsulfuron, Imazosulfuron, Thenylchlor,Alachlor, Pretilachlor, Clomeprop, Etobenzanid, Mefenacet, Flufenacet,Fentrazamide, Pendimethalin, Bifenox, Acifluorfen, Lactfen,Cyhalofop-butyl, Ioxynil, Bromobutide, Alloxydim, Sethoxydim,Napropamide, Indanofan, Pyrazolate, Benzofenap, Pyraflufen-ethyl,Imazapyr, Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat,Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn, Triaziflam,Benfuresate, Fluthiacet-methyl, Quizalofop-ethyl, Bentazone,Oxaziclomefone, Azafenidin, Benzobicyclon, Calcium peroxide, etc.

As to the biotic pesticides, the same effect as above can be expected byusing the agrohorticultural agent of the present invention in admixturewith, for example, viral formulations obtained from Nuclear polyhedrosisvirus (NPV), Granulosis virus (GV), Cytoplasmic polyhedrosis virus(CPV), Entomopox virus (EPV), etc.; microbial pesticides utilized asinsecticides or nematicides, such as Monacrosporium phymatophagum,Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans,etc.; microbial pesticides utilized as fungicides, such as Trichodermalignorum, Agrobacterium radiobacter, nonpathogenic Erwinia carotovora,Bacillus subtilis, etc.; and biotic pesticides utilized as herbicides,such as Xanthomonas campestris, etc.

In addition, the agrohorticultural agent of the present invention can beused in combination with biotic pesticides including natural enemiessuch as Parasitic wasp (Encarsia formosa), Parasitic wasp (Aphidiuscolemani), Gall-mildge (Aphidoletes aphidimyza), Parasitic wasp(Diglyphus isaea), Parasitic mite (Dacnusa sibirica), Predatory mite(Phytoseiulus persimilis), Predatory mite (Amblyseius cucumeris),Predatory bug (Orius sauteri), etc.; microbial pesticides such asBeauveria brongniartii, etc.; and pheromones such as (Z)-10-tetradecenylacetate, (E,Z)-4,10-tetradecadieniel acetate, (Z)-8-dodecenyl acetate,(Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one,14-methyl-1-octadecene, etc.

EXAMPLES

The representative Examples of the present invention are shown below,which are not to be construed as limitative.

Example 1 Production of 4-(4-t-butylbenzyloxy)-5-methoxypyrimidine(compound No. 1-1)

To a solution of 4-chloro-5-methoxypyrimidine (1.5 g, 10.3 mmol)described in Journal of the Chemical Society (1960), 4590, and4-t-butylbenzylalcohol (2.55 g, 15.6 mmol) in dimethylacetamide (10 mL)was added sodium hydride (0.625 g, 15.6 mmol) at 0° C., and the mixturewas stirred at room temperature for 3 hrs. The reaction mixture waspoured into ice water, and extracted with ethyl acetate. The organiclayer was dried over anhydrous magnesium sulfate, and the solvent wasconcentrated under reduced pressure. The residue was purified by silicagel column chromatography to give4-(4-t-butylbenzyloxy)-5-methoxypyrimidine (2.16 g).

yield: 77%

property: melting point 58-59° C.

Example 2 Production of4-(4-trifluoromethylbenzyloxy)-5-phenoxypyrimidine (compound No. 1-95)

To a solution of 4-chloro-5-phenoxypyrimidine (0.4 g, 1.9 mmol)described in JP-A-49-92080 and 4-trifluoromethylbenzylalcohol (0.36 g,2.0 mmol) in dimethylacetamide (7 m) was added sodium hydride (0.093 g,2.3 mmol) at 0° C., and the mixture was stirred at room temperature for3 hrs. The reaction mixture was poured into ice water, and the mixturewas extracted with ethyl acetate. The organic layer was dried overanhydrous magnesium sulfate, and the solvent was concentrated underreduced pressure. The residue was purified by silica gel columnchromatography to give4-(4-trifluoromethylbenzyloxy)-5-phenoxypyrimidine (0.60 g).

yield: 85%

melting point: 56-57° C.

Typical formulation examples and experimental example of the presentinvention are described below but they should not be construed aslimiting the scope of the invention.

As used in the examples, the terms “part” and “parts” means parts byweight.

Formulation Example 1

Compound of the present invention 10 parts Xylene 70 partsN-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl 10parts ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate is prepared by mixing uniformly the aboveingredients to effect dissolution.

Formulation Example 2

Compound of the present invention  3 parts Clay powder 82 partsDiatomaceous earth powder 15 parts

A dust is prepared by mixing uniformly and grinding the aboveingredients.

Formulation Example 3

Compound of the present invention 5 parts Mixed powder of bentonite andclay 90 parts  Calcium ligninsulfonate 5 parts

Granules are prepared by mixing the above ingredients uniformly, andkneading the resulting mixture together with a suitable amount of water,followed by granulation and drying.

Formulation Example 4

Compound of the present invention 20 parts Mixture of kaolin andsynthetic 75 parts high-dispersion silicic acid Mixture ofpolyoxyethylene nonylphenyl  5 parts ether and calciumalkylbenzenesulfonate

A wettable powder is prepared by mixing uniformly and grinding the aboveingredients.

Experimental Example 1 Control Efficacy Against Green Peach Aphid (Myzuspersicae)

A Chinese cabbage plant was planted in each of plastic pots with adiameter of 8 cm and a height of 8 cm and green peach aphids werepropagated on the plant, after which the parasites in each pot werecounted. Each pymidine derivative of the general formula (I) or a saltthereof of the present invention was dispersed in and diluted with waterto obtain a 500 ppm liquid chemical. The stalks and leaves of the pottedChinese cabbage plants were sprayed with the liquid chemical andair-dried, and then the pots were stored in a greenhouse. Six days afterthe spraying, green peach aphids parasitic on each Chinese cabbage plantwere counted and the control efficacy degree was calculated by thefollowing equation, whereby the insecticidal effect was judged accordingto the criterion shown below.Control efficacy=100−{(T×Ca)/(Ta×C)}×100

-   Ta: number of parasites before spraying in treated group,-   T: number of parasites after spraying in treated group,-   Ca: number of parasites before spraying in untreated group,-   C: number of parasites after spraying in untreated group.-   A . . . control efficacy 100%-   B . . . control efficacy 99%-90%-   C . . . control efficacy 89%-80%-   D . . . control efficacy 79%-50%

Experimental Example 2 Insecticidal Effect on Brown Rice Planthopper(Nilaparvata lugens)

Each benzyloxypymidine derivative of the general formula (I) or a saltthereof of the present invention was dispersed in and diluted with waterto obtain a 500 ppm liquid chemical. Rice seedlings (cultivar:Nihonbare) were immersed in the liquid chemical for 30 seconds andair-dried, after which each seedling was placed in a glass test tube andinoculated with 10 third-instar nymphs of brown rice planthopper, andthe test tube was plugged with a cotton plug. Eight days after theinoculation, the dead and alive were counted. The mortality wascalculated by the following equation and the control effect was judgedaccording to the criterion described below.

${{Corrected}\mspace{14mu}{mortality}\mspace{14mu}(\%)} = {\frac{\begin{matrix}{( {{survival}\mspace{14mu}{rate}\mspace{14mu}{in}\mspace{14mu}{untreated}\mspace{14mu}{group}} ) -} \\( {{survival}\mspace{14mu}{rate}\mspace{14mu}{in}\mspace{14mu}{treated}\mspace{14mu}{group}} )\end{matrix}}{( {{survival}\mspace{14mu}{rate}\mspace{14mu}{in}\mspace{14mu}{untreated}\mspace{14mu}{group}} )} \times 100}$diagnostic criteria . . . Same as in Experimental Example 1.

As a result, among the benzyloxypyrimidine derivatives of the presentinvention represented by the formula (I), the compounds of compound Nos.1-1, 1-2, 1-3, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-14, 1-15, 1-16, 1-18,1-21, 1-23, 1-28, 1-30, 1-35, 1-39, 1-41, 1-42, 1-62, 1-63, 1-70, 1-72,1-74, 1-76, 1-78, 1-80, 1-81, 1-83, 1-86, 1-88, 1-90, 1-92, 1-94, 1-95,1-103, 1-107, 1-108, 1-109, 1-110, 1-113, 1-114, 1-115, 1-116, 1-120,1-122, 1-124, 1-129, 1-130, 1-134, 1-135, 1-138, 1-139, 1-141, 1-142,1-143, 1-144, 1-145, 1-147, 1-148, 1-156, 1-157, 1-205, 1-207, 1-208,1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218,1-219, 1-222, 1-223, 1-224, 1-225, 1-226, 1-227, 1-228, 1-230, 1-231,1-242, 1-243, 1-244, 1-246, 1-247, 1-248, 1-249, 1-250, 1-251, 1-252,1-253, 1-254, 1-256, 1-257, 1-258, 1-259, 1-260, 1-264, 1-265, 1-266,1-267, 1-270, 2-2, 2-3, 3-1, 3-2, 3-4, 3-5, 3-6, 3-7, 3-9, 3-11, 3-12,3-13, 3-14, 3-16, 3-18, 3-19, 3-20, 3-21, 3-22, 3-24, 3-25, 3-26, 3-27,3-28, 3-29, 3-30, 3-31, 3-32, 3-33, 3-34, 3-36, 3-37, 3-38, 3-39, 3-40,3-41, 3-42, 3-43, 3-44, 3-45, 3-46, 3-47, 3-49, 3-52, 3-54, 3-56, 3-57,3-58, 3-60, 3-61, 3-62, 3-64, 3-65, 3-66, 3-67, 3-68, 3-69, 3-70, 3-71,3-72, 3-74, 3-75, 3-76, 3-77, 3-78, 3-81, 3-84, 3-85, 3-86, 3-88, 3-91,3-93, 3-94, 3-96, 3-97, 3-103, 3-105, 3-107, 3-108, 3-109, 3-110, 3-112,3-113, 3-114, 3-117, 3-120, 3-121, 3-122, 3-124, 3-125, 3-127, 3-129,3-130, 3-131, 3-134, 3-135, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144,3-145, 3-146, 3-147, 3-148, 3-152, 3-153, 3-154, 3-157, 3-158, 3-159,3-164, 3-168, 3-169, 3-170, 3-171, 3-172, 3-173, 3-174, 3-176, 3-177,3-179, 3-180, 3-182, 3-183, 3-184, 3-185, 3-187, 3-188, 3-189, 3-190,3-191, 3-192, 3-194, 3-199, 3-206, 3-207, 3-208, 3-209, 3-213, 3-214,3-215, 3-216, 3-217, 3-218, 3-219, 3-223, 3-224, 3-229, 3-230, 3-235,3-253, 3-254, 4-10, 4-55, 4-56 and 4-57 showed insecticidal effects ofnot less than D against green peach aphid, and particularly, thecompounds of 1-1, 1-3, 1-7, 1-10, 1-15, 1-21, 1-23, 1-35, 1-62, 1-78,1-83, 1-103, 1-108, 1-116, 1-120, 1-122, 1-138, 1-205, 1-209, 1-210,1-211, 1-216, 1-217, 1-218, 1-219, 1-223, 1-226, 1-230, 1-244, 2-3, 3-1,3-2, 3-6, 3-7, 3-9, 3-11, 3-13, 3-19, 3-22, 3-31, 3-33, 3-34, 3-36,3-37, 3-42, 3-45, 3-54, 3-56, 3-57, 3-58, 3-60, 3-61, 3-62, 3-64, 3-67,3-69, 3-70, 3-72, 3-74, 3-75, 3-77, 3-81, 3-91, 3-97, 3-103, 3-107,3-108, 3-114, 3-117, 3-121, 3-131, 3-139, 3-140, 3-142, 3-143, 3-145,3-157, 3-179, 3-180, 3-182, 3-185, 3-187, 3-194, 3-214, 3-215, 3-216,3-218, 3-219, 3-229, 3-254, 4-55, 4-56 and 4-57 showed superiorinsecticidal effects of A.

Against brown rice planthopper, moreover, the compounds of compound Nos.1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-14, 1-15, 1-16,1-18, 1-20, 1-21, 1-23, 1-26, 1-28, 1-30, 1-35, 1-39, 1-40, 1-41, 1-42,1-62, 1-63, 1-64, 1-70, 1-72, 1-74, 1-76, 1-78, 1-80, 1-81, 1-83, 1-86,1-88, 1-90, 1-92, 1-94, 1-95, 1-98, 1-99, 1-103, 1-107, 1-108, 1-109,1-110, 1-113, 1-114, 1-116, 1-120, 1-122, 1-124, 1-129, 1-130, 1-135,1-138, 1-139, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148,1-156, 1-157, 1-192, 1-195, 1-205, 1-207, 1-208, 1-209, 1-210, 1-212,1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-222, 1-223, 1-224,1-227, 1-228, 1-230, 1-231, 1-240, 1-242, 1-243, 1-244, 1-246, 1-247,1-248, 1-249, 1-250, 1-251, 1-252, 1-253, 1-254, 1-256, 1-257, 1-258,1-259, 1-260, 1-261, 1-264, 1-265, 1-266, 1-267, 1-270, 1-282, 1-289,1-290, 2-2, 2-3, 2-6, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-11,3-12, 3-13, 3-22, 3-24, 3-25, 3-26, 3-28, 3-29, 3-30, 3-31, 3-32, 3-33,3-34, 3-37, 3-38, 3-39, 3-40, 3-41, 3-42, 3-43, 3-44, 3-45, 3-46, 3-47,3-48, 3-49, 3-52, 3-54, 3-56, 3-57, 3-58, 3-60, 3-61, 3-62, 3-63, 3-64,3-65, 3-66, 3-67, 3-68, 3-69, 3-70, 3-71, 3-72, 3-74, 3-75, 3-76, 3-77,3-79, 3-81, 3-85, 3-86, 3-88, 3-89, 3-90, 3-91, 3-92, 3-93, 3-94, 3-97,3-99, 3-102, 3-103, 3-107, 3-108, 3-109, 3-112, 3-113, 3-114, 3-117,3-120, 3-122, 3-123, 3-124, 3-125, 3-126, 3-127, 3-128, 3-130, 3-131,3-132, 3-136, 3-139, 3-140, 3-142, 3-143, 3-145, 3-146, 3-147, 3-148,3-152, 3-153, 3-154, 3-156, 3-157, 3-158, 3-159, 3-164, 3-168, 3-169,3-171, 3-172, 3-173, 3-174, 3-175, 3-176, 3-179, 3-180, 3-181, 3-182,3-183, 3-184, 3-185, 3-186, 3-187, 3-188, 3-190, 3-191, 3-192, 3-194,3-199, 3-206, 3-207, 3-208, 3-209, 3-211, 3-213, 3-214, 3-216, 3-217,3-218, 3-219, 3-223, 3-224, 3-235, 4-10, 4-11, 4-12, 4-55, 4-56 and 4-57showed superior insecticidal effects of A.

Experimental Example 3 Acaricidal Effect on Cattle Tick (Haemaphysalislongicornis)

An absorbent cotton was placed on the basement of a glass bottle(diameter 3 cm×height 4.5 cm). The pyrimidine derivative of the presentinvention represented by the formula (I) or a salt thereof was dispersedin water to give a diluted drug solution (100 ppm). The drug solution (2ml) was added dropwise. Cattle ticks were inoculated by 5 each, and thebottle was capped with a mesh. After 4 days from the inoculation, thedead ticks and live ticks were counted, and the corrected mortality wascalculated by the following formula.corrected mortality (%)=(survival rate in untreated group−survival ratein treated group)/(survival rate in untreated group)×100Diagnostic criteria . . . as defined in Experimental Example 1

As a result, among the benzyloxypyrimidine derivatives of the presentinvention represented by the formula (I), compound Nos. 1-1, 1-5, 1-14,1-15, 1-62, 1-78, 1-103, 1-138, 1-190, 1-207, 1-209 and 1-212 showedacaricidal effects of not less than D against cattle tick.

Industrial Applicability

The benzyloxypyrimidine derivative of the present invention or a saltthereof has a superior effect as an agrohorticultural insecticide. Onthe other hand, the derivative shows an effect on pests being parasiticin pet animals such as dogs and cats, and domestic animals such ascattle, sheep and the like.

This application is based on patent application Nos. 287777/2010 and181052/2011 filed in Japan, the contents of which are herebyincorporated by reference.

The invention claimed is:
 1. A benzyloxypyrimidine derivativerepresented by the formula (I):

wherein R¹ is (a1) a hydrogen atom; (a2) a (C₁-C₆)alkyl group; (a3) a(C₃-C₇)cycloalkyl group (said cycloalkyl group is optionally fused witha benzene ring); (a4) a (C₂-C₆)alkenyl group; (a5) a (C₂-C₆)alkynylgroup; (a6) a halo(C₁-C₆)alkyl group; (a7) a halo(C₃-C₆)cycloalkylgroup; (a9) a halo(C₂-C₆)alkynyl group; (a10) a(C₁-C₆)alkoxy(C₁-C₆)alkyl group; (a11) a (C₃-C₆)cycloalkyl(C₁-C₆)alkylgroup; (a12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; (a13) a(C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group; (a14) a(C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group; (a15) ahalo(C₁-C₆)alkoxy(C₁-C₆)alkyl group; (a16) ahalo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group; (a17) ahalo(C₁-C₆)alkylthio(C₁-C₆)alkyl group; (a18) ahalo(C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group; (a19) ahalo(C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group; (a20) a(C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group; (a21) ahalo(C₁-C₆)alkoxyhalo(C₁-C₆)alkyl group; (a22) an aryl(C₁-C₆)alkylgroup; (a23) an aryl(C₁-C₆)alkyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group wherein R⁴and R⁵ may be the same or different and each is a hydrogen atom, a(C₁-C₆)alkyl group, a (C₃-C₆)cycloalkyl group, a (C₂-C₆)alkenyl group, a(C₂-C₆)alkynyl group, a (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group, ahalo(C₁-C₆)alkyl group, a halo(C₃-C₆)cycloalkyl group, ahalo(C₂-C₆)alkenyl group, a halo(C₂-C₆)alkynyl group, ahalo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group, a phenyl group, or aphenyl(C₁-C₆)alkyl group; (a24) a cyano(C₁-C₆)alkyl group; (a25) anitro(C₁-C₆)alkyl group; (a26) a R⁴(R⁵)N(C₁-C₆)alkyl group wherein R⁴and R⁵ are as defined above; (a27) a (R⁴)OC(C₁-C₆)alkyl group wherein R⁴is as defined above; (a28) a (R⁴)O₂C(C₁-C₆)alkyl group wherein R⁴ is asdefined above; (a29) a R⁴(R⁵)NCO(C₁-C₆)alkyl group wherein R⁴ and R⁵ areas defined above; (a30) an aryl group; (a31) an aryl group having, onthe ring, the same or different 1 to 5 substituents selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a(C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, and (t) a phenoxygroup; (a32) an arylsulfonyl group; (a33) an arylsulfonyl group having,on the ring, the same or different 1 to 5 substituents selected from (a)a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formylgroup, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a(C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above; (a34) anarylcarbonyl group; (a35) an arylcarbonyl group having, on the ring, thesame or different 1 to 5 substituents selected from (a) a halogen atom,(b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxygroup, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above; (a36) anarylthio(C₁-C₆)alkyl group; (a37) an arylthio(C₁-C₆)alkyl group having,on the ring, the same or different 1 to 5 substituents selected from (a)a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formylgroup, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a(C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above; (a38) anarylsulfinyl(C₁-C₆)alkyl group; (a39) an arylsulfinyl(C₁-C₆)alkyl grouphaving, on the ring, the same or different 1 to 5 substituents selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group,(g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above; (a40) anarylsulfonyl(C₁-C₆)alkyl group; (a41) an arylsulfonyl(C₁-C₆)alkyl grouphaving, on the ring, the same or different 1 to 5 substituents selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group,(g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above; (a42) anarylcarbonyloxy(C₁-C₆)alkyl group; (a43) an arylcarbonyloxy(C₁-C₆)alkylgroup having, on the ring, the same or different 1 to 5 substituentsselected from (a) a halogen atom, (b) a cyano group, (c) a nitro group,(d) a formyl group, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkylgroup, (g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above; (a44) a(C₁-C₆)alkylcarbonyl group; (a45) a (C₁-C₆)alkoxycarbonyl group; (a47) aR⁴(R⁵)N carbonyloxy(C₁-C₆)alkyl group wherein R⁴ and R⁵ are as definedabove; (a48) a tri(C₁-C₆)alkylsilyl group wherein the alkyl groups maybe the same or different; (a49) a (C₁-C₆)alkoxy(C₁-C₆)alkoxy(C₁-C₆)alkylgroup; (a50) a (C₁-C₆)alkoxycarbonyloxy(C₁-C₆)alkyl group; (a51) a(C₁-C₆)alkyl(C₁-C₆)sulfonyl group; (a52) a heterocyclic group; (a53) aheterocyclic group having, on the ring, the same or different 1 to 5substituents selected from (a) a halogen atom, (b) a cyano group, (c) anitro group, (d) a formyl group, (e) a (C₁-C₆)alkyl group, (f) ahalo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴ andR⁵ are as defined above, and (t) an oxo group; (a54) aheterocyclyl(C₁-C₆)alkyl group; (a55) a heterocyclyl(C₁-C₆)alkyl grouphaving, on the ring, the same or different 1 to 5 substituents selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆)alkyl group, (l) a halo(C₁-C₆)alkyl group,(g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, and (t) an oxogroup; (a56) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkylgroups of the tri(C₁-C₆)alkylsilyl may be the same or different; or(a57) a R⁴(R⁵)NCO group wherein R⁴ and R⁵ are as defined above, A is—O—, —S—, —SO— or —SO₂—, R² and R³ may be the same or different, andeach is (b1) a hydrogen atom; (b2) a (C₁-C₆)alkyl group; (b3) a(C₃-C₆)cycloalkyl group; (b4) a (C₂-C₆)alkenyl group; (b5) a(C₂-C₆)alkynyl group; (b6) a halo(C₁-C₆)alkyl group; (b7) ahalo(C₃-C₆)cycloalkyl group; (b8) a halo(C₂-C₆)alkenyl group; (b9) ahalo(C₂-C₆)alkynyl group; (b10) a (C₃-C₆)cycloalkyl(C₁-C₆)alkyl group;(b11) a (C₁-C₆)alkoxy(C₁-C₆)alkyl group; (b12) a(C₁-C₆)alkylthio(C₁-C₆)alkyl group; or (b13) a (C₁-C₆)alkoxycarbonylgroup, X may be the same or different, and each is (c1) a hydrogen atom;(c2) a halogen atom; (c3) a hydroxyl group; (c4) a cyano group; (c5) anitro group; (c6) a N(R⁴)(R⁵) group wherein R⁴ and R⁵ are as definedabove; (c7) a N(R⁴)CO(R⁵) group wherein R⁴ and R⁵ are as defined above;(c8) a N(R⁴)SO₂(R⁵) group wherein R⁴ and R⁵ are as defined above; (c9) aN(R⁴)CO₂(R⁵) group wherein R⁴ and R⁵ are as defined above; (c10) aCO(R⁴) group wherein R⁴ is as defined above; (c11) a CO₂(R⁴) groupwherein R⁴ is as defined above; (c12) a CON(R⁴)(R⁵) group wherein R⁴ andR⁵ are as defined above; (c13) a C(R⁴)═NOR⁵ group wherein R⁴ and R⁵ areas defined above; (c14) a (C₁-C₁₂)alkyl group; (c15) a (C₂-C₁₂)alkenylgroup; (c16) a (C₂-C₁₂)alkynyl group; (c17) a (C₃-C₁₂)cycloalkyl group;(c18) a halo(C₁-C₁₂)alkyl group; (c19) a halo(C₂-C₁₂)alkenyl group;(c20) a halo(C₂-C₁₂)alkynyl group; (c21) a halo(C₃-C₁₂)cycloalkyl group;(c22) a tri(C₁-C₁₂)alkylsilyl group wherein the alkyl groups may be thesame or different; (c23) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent; (c24) a (C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkyl group; (c25) ahalo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkyl group; (c26) a(C₃-C₁₂)cycloalkyl(C₃-C₁₂)cycloalkyl group; (c27) a (C₁-C₁₂)alkoxygroup; (c28) a (C₂-C₁₂)alkenyloxy group; (c29) a (C₂-C₁₂)alkynyloxygroup; (c30) a (C₃-C₁₂)cycloalkyloxy group (said cycloalkyl isoptionally fused with a benzene ring); (c31) a halo(C₁-C₁₂)alkoxy group;(c32) a halo(C₂-C₁₂)alkenyloxy group; (c33) a halo(C₂-C₁₂)alkynyloxygroup; (c34) a halo(C₃-C₁₂)cycloalkyloxy group (said cycloalkyl isoptionally fused with a benzene ring); (c35) a(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkoxy group; (c36) ahalo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkoxy group; (c37) a(C₁-C₆)alkoxy(C₁-C₆)alkyl group; (c38) a halo(C₁-C₆)alkoxy(C₁-C₆)alkoxygroup; (c39) a (C₁-C₆)alkoxyhalo(C₁-C₆)alkoxy group; (c40) ahalo(C₁-C₆)alkoxyhalo(C₁-C₆)alkoxy group; (c41) a mercapto group; (c42)a (C₁-C₁₂)alkylthio group; (c43) a (C₂-C₁₂)alkenylthio group; (c44) a(C₂-C₁₂)alkynylthio group; (c45) a (C₃-C₁₂)cycloalkylthio group; (c46) ahalo(C₁-C₁₂)alkylthio group; (c47) a halo(C₂-C₁₂)alkenylthio group;(c48) a halo(C₂-C₁₂)alkynylthio group; (c49) ahalo(C₃-C₁₂)cycloalkylthio group; (c50) a(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylthio group; (c51) ahalo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylthio group; (c52) a(C₁-C₆)alkoxy(C₁-C₆)alkylthio group; (c53) ahalo(C₁-C₆)alkoxy(C₁-C₆)alkylthio group; (c54) a(C₁-C₆)alkoxyhalo(C₁-C₆)alkylthio group; (c55) ahalo(C₁-C₆)alkoxyhalo(C₁-C₆)alkylthio group; (c56) a(C₁-C₁₂)alkylsulfinyl group; (c57) a (C₂-C₁₂)alkenylsulfinyl group;(c58) a (C₂-C₁₂)alkynylsulfinyl group; (c59) a(C₃-C₁₂)cycloalkylsulfinyl group; (c60) a halo(C₁-C₁₂)alkylsulfinylgroup; (c61) a halo(C₂-C₁₂)alkenylsulfinyl group; (c62) ahalo(C₂-C₁₂)alkynylsulfinyl group; (c63) ahalo(C₃-C₁₂)cycloalkylsulfinyl group; (c64) a(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfinyl group; (c65) ahalo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfinyl group; (c66) a(C₁-C₁₂)alkylsulfonyl group; (c67) a (C₂-C₁₂)alkenylsulfonyl group;(c68) a (C₂-C₁₂)alkynylsulfonyl group; (c69) a(C₃-C₁₂)cycloalkylsulfonyl group; (c70) a halo(C₁-C₁₂)alkylsulfonylgroup; (c71) a halo(C₂-C₁₂)alkenylsulfonyl group; (c72) ahalo(C₂-C₁₂)alkynylsulfonyl group; (c73) ahalo(C₃-C₁₂)cycloalkylsulfonyl group; (c74) a(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfonyl group; (c75) ahalo(C₃-C₁₂)cycloalkyl(C₁-C₁₂)alkylsulfonyl group; (c76) an aryl group;(c77) an aryl group having, on the ring, the same or different 1 to 5substituents selected from (a) a halogen atom, (b) a cyano group, (c) anitro group, (d) a (C₁-C₆)alkyl group, (e) a halo(C₁-C₆)alkyl group, (f)a (C₁-C₆)alkoxy group, (g) a halo(C₁-C₆)alkoxy group, (h) a(C₂-C₆)alkenyloxy group, (i) a halo(C₂-C₆)alkenyloxy group, (j) a(C₂-C₆)alkynyloxy group, (k) a halo(C₂-C₆)alkynyloxy group, (l) a(C₃-C₆)cycloalkoxy group, (m) a halo(C₃-C₆)cycloalkoxy group, (n) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (o) ahalo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a (C₁-C₆)alkylthio group,(q) a halo(C₁-C₆)alkylthio group, (r) a (C₁-C₆)alkylsulfinyl group, (s)a halo(C₁-C₆)alkylsulfinyl group, (t) a (C₁-C₆)alkylsulfonyl group, (u)a halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and R⁵are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵ are asdefined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are as definedabove, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as defined above,(z) a COR⁴ group wherein R⁴ is as defined above, (aa) a CO₂R⁴ groupwherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group wherein R⁴ and R⁵are as defined above, and (cc) a C(R⁴)NOR⁵ group wherein R⁴ and R⁵ areas defined above; (c78) an aryl(C₁-C₆)alkyl group; (c79) anaryl(C₁-C₆)alkyl group having, on the ring, the same or different 1 to 5substituents selected from (a) a halogen atom, (b) a cyano group, (c) anitro group, (d) a (C₁-C₆)alkyl group, (e) a halo(C₁-C₆)alkyl group, (f)a (C₁-C₆)alkoxy group, (g) a halo(C₁-C₆)alkoxy group, (h) a(C₂-C₆)alkenyloxy group, (i) a halo(C₂-C₆)alkenyloxy group, (j) a(C₂-C₆)alkynyloxy group, (k) a halo(C₂-C₆)alkynyloxy group, (l) a(C₃-C₆)cycloalkoxy group, (m) a halo(C₃-C₆)cycloalkoxy group, (n) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (o) ahalo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a (C₁-C₆)alkylthio group,(q) a halo(C₁-C₆)alkylthio group, (r) a (C₁-C₆)alkylsulfinyl group, (s)a halo(C₁-C₆)alkylsulfinyl group, (t) a (C₁-C₆)alkylsulfonyl group, (u)a halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and R⁵are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵ are asdefined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are as definedabove, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as defined above,(z) a COR⁴ group wherein R⁴ is as defined above, (aa) a CO₂R⁴ groupwherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group wherein R⁴ and R⁵are as defined above, and (cc) a C(R⁴)NOR⁵ group wherein R⁴ and R⁵ areas defined above; (c80) an aryloxy group; (c81) an aryloxy group having,on the ring, the same or different 1 to 5 substituents selected from (a)a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C₁-C₆)alkylgroup, (e) a halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) ahalo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) ahalo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) ahalo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) ahalo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxygroup, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a(C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a(C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl group, (t) a(C₁-C₆)alkylsulfonyl group, (u) a halo(C₁-C₆)alkylsulfonyl group, (v) anN(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, (w) an N(R⁴)COR⁵group wherein R⁴ and R⁵ are as defined above, (x) an N(R⁴)CO₂R⁵ groupwherein R⁴ and R⁵ are as defined above, (y) an N(R⁴)SO₂R⁵ group whereinR⁴ and R⁵ are as defined above, (z) a COR⁴ group wherein R⁴ is asdefined above, (aa) a CO₂R⁴ group wherein R⁴ is as defined above, (bb) aCON(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, and (cc) aC(R⁴)NOR⁵ group wherein R⁴ and R⁵ are as defined above; (c82) anaryloxy(C₁-C₆)alkyl group; (c83) an aryloxy(C₁-C₆)alkyl group having, onthe ring, the same or different 1 to 5 substituents selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a (C₁-C₆)alkylgroup, (e) a halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) ahalo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) ahalo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) ahalo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) ahalo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxygroup, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a(C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a(C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl group, (t) a(C₁-C₆)alkylsulfonyl group, (u) a halo(C₁-C₆)alkylsulfonyl group, (v) anN(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, (w) an N(R⁴)COR⁵group wherein R⁴ and R⁵ are as defined above, (x) an N(R⁴)CO₂R⁵ groupwherein R⁴ and R⁵ are as defined above, (y) an N(R⁴)SO₂R⁵ group whereinR⁴ and R⁵ are as defined above, (z) a COR⁴ group wherein R⁴ is asdefined above, (aa) a CO₂R⁴ group wherein R⁴ is as defined above, (bb) aCON(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, and (cc) aC(R⁴)NOR⁵ group wherein R⁴ and R⁵ are as defined above; (c84) anarylthio group; (c85) an arylthio group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) ahalo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) ahalo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) ahalo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) ahalo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) ahalo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxygroup, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a(C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a(C₂-C₆)alkylsulfinyl group, (s) a halo(C₂-C₆)alkylsulfinyl group, (t) a(C₁-C₆)alkylsulfonyl group, (u) a halo(C₁-C₆)alkylsulfonyl group, (v) anN(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, (w) an N(R⁴)COR⁵group wherein R⁴ and R⁵ are as defined above, (x) an N(R⁴)CO₂R⁵ groupwherein R⁴ and R⁵ are as defined above, (y) an N(R⁴)SO₂R⁵ group whereinR⁴ and R⁵ are as defined above, (z) a COR⁴ group wherein R⁴ is asdefined above, (aa) a CO₂R⁴ group wherein R⁴ is as defined above, (bb) aCON(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, and (cc) aC(R⁴)NOR⁵ group wherein R⁴ and R⁵ are as defined above; (c86) ahalo(C₁-C₆)alkylenedioxy group; (c87) a (C₁-C₆)alkoxy(C₁-C₆)alkoxygroup; (c88) a (C₃-C₈)alkylene group; (c89) a(C₁-C₆)alkyl(C₃-C₈)alkylene group; (c90) a tri(C₁-C₁₂)alkylsilyloxygroup wherein the alkyl groups may be the same or different; (c91) atri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkoxy group wherein the alkyl groups may bethe same or different; (c92) a di(C₁-C₁₂)alkylhalo(C₁-C₆)alkylsilylgroup wherein the alkyl groups may be the same or different; (c93) adi(C₁-C₁₂)alkyl(C₁-C₆)alkylthio(C₁-C₆)alkylsilyl group wherein the alkylgroups may be the same or different; (c94) a di(C₁-C₁₂)alkylhydroxysilylgroup wherein the alkyl groups may be the same or different; (c95) adi(C₁-C₁₂)alkylhydrosilyl group wherein the alkyl groups may be the sameor different; (c96) a di(C₁-C₁₂)alkylphenylsilyl group wherein the alkylgroups may be the same or different; (c97) a(C₁-C₆)alkylthio(C₁-C₆)alkoxy group; (c98) a(C₁-C₆)alkylsulfinyl(C₁-C₆)alkoxy group; (c99) a(C₁-C₆)alkylsulfonyl(C₁-C₆)alkoxy group; (c100) a(C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy group; (c101) a(C₁-C₆)alkylcarbonyl(C₁-C₆)alkoxy group; (c102) a cyano(C₁-C₆)alkoxygroup; (c103) an aryl(C₁-C₆)alkoxy group wherein the alkoxy moiety maybe halogenated; (c104) an aryl(C₁-C₆)alkoxy group wherein the alkoxymoiety may be halogenated, which has, on the ring, the same or different1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group,(c) a nitro group, (d) a (C₁-C₆)alkyl group, (e) a halo(C₁-C₆)alkylgroup, (f) a (C₁-C₆)alkoxy group, (g) a halo(C₁-C₆)alkoxy group, (h) a(C₂-C₆)alkenyloxy group, (i) a halo(C₂-C₆)alkenyloxy group, (j) a(C₂-C₆)alkynyloxy group, (k) a halo(C₂-C₆)alkynyloxy group, (l) a(C₃-C₆)cycloalkoxy group, (m) a halo(C₃-C₆)cycloalkoxy group, (n) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (o) ahalo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a (C₁-C₆)alkylthio group,(q) a halo(C₁-C₆)alkylthio group, (r) a (C₂-C₆)alkylsulfinyl group, (s)a halo(C₂-C₆)alkylsulfinyl group, (t) a (C₁-C₆)alkylsulfonyl group, (u)a halo(C₁-C₆)alkylsulfonyl group, (v) an N(R⁴)R⁵ group wherein R⁴ and R⁵are as defined above, (w) an N(R⁴)COR⁵ group wherein R⁴ and R⁵ are asdefined above, (x) an N(R⁴)CO₂R⁵ group wherein R⁴ and R⁵ are as definedabove, (y) an N(R⁴)SO₂R⁵ group wherein R⁴ and R⁵ are as defined above,(z) a COR⁴ group wherein R⁴ is as defined above, (aa) a CO₂R⁴ groupwherein R⁴ is as defined above, (bb) a CON(R⁴)R⁵ group wherein R⁴ and R⁵are as defined above, and (cc) a C(R⁴)NOR⁵ group wherein R⁴ and R⁵ areas defined above; (c105) a hydroxy(C₁-C₆)alkyl group; (c106) a(C₁-C₆)alkylthio(C₁-C₆)alkylcarbonyl group; (c107) a(C₁-C₆)alkylthio(C₁-C₆)alkyl group; (c108) atri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkylthio group wherein the alkyl groups ofthe tri(C₁-C₁₂)alkylsilyl may be the same or different; (c109) atri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkylsulfinyl group wherein the alkyl groupsof the tri(C₁-C₁₂)alkylsilyl may be the same or different; (c110) atri(C₁-C₁₂)alkylsilyl(C₁-C₆)alkylsulfonyl group wherein the alkyl groupsof the tri(C₁-C₁₂)alkylsilyl may be the same or different; (c111) aR⁴(R⁵)N(C₁-C₆)alkyl group wherein R⁴ and R⁵ are as defined above; (c112)a heterocyclic group; (c113) a heterocyclic group having, on the ring,the same or different 1 to 5 substituents selected from (a) a halogenatom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxygroup, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c114)a heterocyclyloxy group; (c115) a heterocyclyloxy group having, on thering, the same or different 1 to 5 substituents selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a(C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c116)a heterocyclylthio group; (c117) a heterocyclylthio group having, on thering, the same or different 1 to 5 substituents selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a(C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c118)a heterocyclylsulfinyl group; (c119) a heterocyclylsulfinyl grouphaving, on the ring, the same or different 1 to 5 substituents selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group,(g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c120)a heterocyclylsulfonyl group; (c121) a heterocyclylsulfonyl grouphaving, on the ring, the same or different 1 to 5 substituents selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group,(g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c122)a heterocyclyl(C₁-C₆)alkyloxy group; (c123) a heterocyclylalkyloxy grouphaving, on the ring, the same or different 1 to 5 substituents selectedfrom (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) aformyl group, (e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group,(g) a (C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c124)a (C₁-C₁₂)alkyl(C₃-C₁₂)cycloalkyl group; (c125) ahalo(C₁-C₁₂)alkyl(C₃-C₁₂)cycloalkyl group; (c126) a(C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group; (c127) adi(C₁-C₁₂)alkylbenzylsilyl group wherein the alkyl groups may be thesame or different; (c128) a heterocyclyl(C₁-C₆)alkyl group; (c129) aheterocyclyl(C₁-C₆)alkyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴ andR⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) atri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of thetri(C₁-C₆)alkylsilyl may be the same or different, (v) atri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups may bethe same or different, and (w) an oxo group, (c130) aheterocyclyloxy(C₁-C₆)alkyl group; or (c131) aheterocyclyloxy(C₁-C₆)alkyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴ andR⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) atri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of thetri(C₁-C₆)alkylsilyl may be the same or different, (v) atri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups may bethe same or different, and (w) an oxo group, or X can form, togetherwith the adjacent R² or R³, (c132) a bicyclo ring, wherein the bicycloring optionally has the same or different one or more substituentsselected from (a) a halogen atom, (b) a (C₁-C₆)alkyl group, (c) ahalo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxy group, (e) ahalo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g) ahalo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) ahalo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group, and(k) a halo(C₁-C₆)alkylsulfonyl group; or X can form, together with theadjacent X on an aromatic ring, (c133) a bicyclo ring or (c134) a fusedring, wherein the bicyclo ring or fused ring optionally has the same ordifferent one or more substituents selected from (a) a halogen atom, (b)a (C₁-C₆)alkyl group, (c) a halo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxygroup, (e) a halo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g)a halo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) ahalo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group, and(k) a halo(C₁-C₆)alkylsulfonyl group, and m is an integer of 0 to 5, orsalts thereof.
 2. The benzyloxypyrimidine derivative of claim 1, whereinm is as defined in claim 1, R¹ is (a1) a hydrogen atom; (a2) a(C₁-C₆)alkyl group; (a3) a (C₃-C₇)cycloalkyl group (said cycloalkylgroup is optionally fused with a benzene ring); (a4) a (C₂-C₆)alkenylgroup; (a5) a (C₂-C₆)alkynyl group; (a6) a halo(C₁-C₆)alkyl group; (a10)a (C₁-C₆)alkoxy(C₁-C₆)alkyl group; (a11) a (C₃-C₆)cycloalkyl(C₁-C₆)alkylgroup; (a12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; (a13) a(C₁-C₆)alkylsulfinyl(C₁-C₆)alkyl group; (a14) a(C₁-C₆)alkylsulfonyl(C₁-C₆)alkyl group; (a16) ahalo(C₃-C₆)cycloalkyl(C₁-C₆)alkyl group; (a22) an aryl(C₁-C₆)alkylgroup; (a23) an aryl(C₁-C₆)alkyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group wherein R⁴and R⁵ are as defined in claim 1; (a24) a cyano(C₁-C₆)alkyl group; (a30)an aryl group; (a31) an aryl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴ andR⁵ are as defined above, and (t) a phenoxy group; (a32) an arylsulfonylgroup; (a33) an arylsulfonyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group wherein R⁴and R⁵ are as defined above; (a34) an arylcarbonyl group; (a35) anarylcarbonyl group having, on the ring, the same or different 1 to 5substituents selected from (a) a halogen atom, (b) a cyano group, (c) anitro group, (d) a formyl group, (e) a (C₁-C₆)alkyl group, (f) ahalo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, and (s) a R⁴(R⁵)N carbonyl group wherein R⁴and R⁵ are as defined above; (a44) a (C₁-C₆)alkylcarbonyl group; (a52) aheterocyclic group; (a53) a heterocyclic group having, on the ring, thesame or different 1 to 5 substituents selected from (a) a halogen atom,(b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxygroup, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, and (t) an oxogroup; (a54) a heterocyclyl(C₁-C₆)alkyl group; (a55) aheterocyclyl(C₁-C₆)alkyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴ andR⁵ are as defined above, and (t) an oxo group; (a56) atri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of thetri(C₁-C₆)alkylsilyl may be the same or different; or (a57) a R⁴(R⁵)NCOgroup wherein R⁴ and R⁵ are as defined above, A is —O—, —S—, —SO— or—SO₂—, R² and R³ may be the same or different and each is (b1) ahydrogen atom; (b2) a (C₁-C₆)alkyl group; (b3) a (C₃-C₆)cycloalkylgroup; (b6) a halo(C₁-C₆)alkyl group; (b11) a (C₁-C₆)alkoxy(C₁-C₆)alkylgroup; (b12) a (C₁-C₆)alkylthio(C₁-C₆)alkyl group; or (b13) a(C₁-C₆)alkoxycarbonyl group, and X may be the same or different and eachis (c1) a hydrogen atom; (c2) a halogen atom; (c5) a nitro group; (c14)a (C₁-C₁₂)alkyl group; (c17) a (C₃-C₁₂)cycloalkyl group; (c18) ahalo(C₁-C₁₂)alkyl group; (c21) a halo(C₃-C₁₂)cycloalkyl group; (c22) atri(C₁-C₁₂)alkylsilyl group wherein the alkyl groups may be the same ordifferent; (c27) a (C₁-C₁₂)alkoxy group; (c30) a (C₃-C₁₂)cycloalkyloxygroup (said cycloalkyl is optionally fused with a benzene ring); (c31) ahalo(C₁-C₁₂)alkoxy group; (c38) a halo(C₁-C₆)alkoxy(C₁-C₆)alkoxy group;(c42) a (C₁-C₁₂)alkylthio group; (c46) a halo(C₁-C₁₂)alkylthio group;(c56) a (C₁-C₁₂)alkylsulfinyl group; (c66) a (C₁-C₁₂)alkylsulfonylgroup; (c80) an aryloxy group; (c81) an aryloxy group having, on thering, the same or different 1 to 5 substituents selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a (C₁-C₆)alkylgroup, (e) a halo(C₁-C₆)alkyl group, (f) a (C₁-C₆)alkoxy group, (g) ahalo(C₁-C₆)alkoxy group, (h) a (C₂-C₆)alkenyloxy group, (i) ahalo(C₂-C₆)alkenyloxy group, (j) a (C₂-C₆)alkynyloxy group, (k) ahalo(C₂-C₆)alkynyloxy group, (l) a (C₃-C₆)cycloalkoxy group, (m) ahalo(C₃-C₆)cycloalkoxy group, (n) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxygroup, (o) a halo(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (p) a(C₁-C₆)alkylthio group, (q) a halo(C₁-C₆)alkylthio group, (r) a(C₁-C₆)alkylsulfinyl group, (s) a halo(C₁-C₆)alkylsulfinyl group, (t) a(C₁-C₆)alkylsulfonyl group, (u) a halo(C₁-C₆)alkylsulfonyl group, (v) anN(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, (w) an N(R⁴)COR⁵group wherein R⁴ and R⁵ are as defined above, (x) an N(R⁴)CO₂R⁵ groupwherein R⁴ and R⁵ are as defined above, (y) an N(R⁴)SO₂R⁵ group whereinR⁴ and R⁵ are as defined above, (z) a COR⁴ group wherein R⁴ is asdefined above, (aa) a CO₂R⁴ group wherein R⁴ is as defined above, (bb) aCON(R⁴)R⁵ group wherein R⁴ and R⁵ are as defined above, and (cc) aC(R⁴)NOR⁵ group wherein R⁴ and R⁵ are as defined above; (c112) aheterocyclic group; (c113) a heterocyclic group having, on the ring, thesame or different 1 to 5 substituents selected from (a) a halogen atom,(b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a(C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxygroup, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c114)a heterocyclyloxy group; (c115) a heterocyclyloxy group having, on thering, the same or different 1 to 5 substituents selected from (a) ahalogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group,(e) a (C₁-C₆)alkyl group, (f) a halo(C₁-C₆)alkyl group, (g) a(C₁-C₆)alkoxy group, (h) a halo(C₁-C₆)alkoxy group, (i) a(C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j) a (C₁-C₆)alkylthio group, (k)a halo(C₁-C₆)alkylthio group, (l) a (C₁-C₆)alkylsulfinyl group, (m) ahalo(C₁-C₆)alkylsulfinyl group, (n) a (C₁-C₆)alkylsulfonyl group, (o) ahalo(C₁-C₆)alkylsulfonyl group, (p) a (C₁-C₆)alkylcarbonyl group, (q) acarboxyl group, (r) a (C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)Ncarbonyl group wherein R⁴ and R⁵ are as defined above, (t) a(C₂-C₆)alkynyl group, (u) a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groupwherein the alkyl groups of the tri(C₁-C₆)alkylsilyl may be the same ordifferent, (v) a tri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein thealkyl groups may be the same or different, and (w) an oxo group; (c130)a heterocyclyloxy(C₁-C₆)alkyl group; or (c131) aheterocyclyloxy(C₁-C₆)alkyl group having, on the ring, the same ordifferent 1 to 5 substituents selected from (a) a halogen atom, (b) acyano group, (c) a nitro group, (d) a formyl group, (e) a (C₁-C₆)alkylgroup, (f) a halo(C₁-C₆)alkyl group, (g) a (C₁-C₆)alkoxy group, (h) ahalo(C₁-C₆)alkoxy group, (i) a (C₃-C₆)cycloalkyl(C₁-C₆)alkoxy group, (j)a (C₁-C₆)alkylthio group, (k) a halo(C₁-C₆)alkylthio group, (l) a(C₁-C₆)alkylsulfinyl group, (m) a halo(C₁-C₆)alkylsulfinyl group, (n) a(C₁-C₆)alkylsulfonyl group, (o) a halo(C₁-C₆)alkylsulfonyl group, (p) a(C₁-C₆)alkylcarbonyl group, (q) a carboxyl group, (r) a(C₁-C₆)alkoxycarbonyl group, (s) a R⁴(R⁵)N carbonyl group wherein R⁴ andR⁵ are as defined above, (t) a (C₂-C₆)alkynyl group, (u) atri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl group wherein the alkyl groups of thetri(C₁-C₆)alkylsilyl may be the same or different, (v) atri(C₁-C₆)alkylsilyl(C₂-C₆)alkynyl group wherein the alkyl groups may bethe same or different, and (w) an oxo group, or X can form, togetherwith the adjacent R² or R³, (c132) a bicyclo ring, wherein the bicycloring optionally has the same or different one or more substituentsselected from (a) a halogen atom, (b) a (C₁-C₆)alkyl group, (c) ahalo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxy group, (e) ahalo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g) ahalo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) ahalo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group, and(k) a halo(C₁-C₆)alkylsulfonyl group; or, X can form, together with theadjacent X on an aromatic ring, (c133) a bicyclo ring or (C134) a fusedring, wherein the bicyclo ring or fused ring optionally has the same ordifferent one or more substituents selected from (a) a halogen atom, (b)a (C₁-C₆)alkyl group, (c) a halo(C₁-C₆)alkyl group, (d) a (C₁-C₆)alkoxygroup, (e) a halo(C₁-C₆)alkoxy group, (f) a (C₁-C₆)alkylthio group, (g)a halo(C₁-C₆)alkylthio group, (h) a (C₁-C₆)alkylsulfinyl group, (i) ahalo(C₁-C₆)alkylsulfinyl group, (j) a (C₁-C₆)alkylsulfonyl group, and(k) a halo(C₁-C₆)alkylsulfonyl group, or salts thereof.
 3. Anagrohorticultural insecticide composition comprising (a) thebenzyloxypyrimidine derivative according to claim 1 or a salt thereof asan active ingredient and (b) an inert carrier.
 4. A method of using anagrohorticultural insecticide, which comprises treating a plant or soilwith the active ingredient of the agrohorticultural insecticideaccording to claim
 3. 5. A method of controlling an agrohorticulturalpest, which comprises treating a plant or soil with an effective amountof the benzyloxypyrimidine derivative according to claim 1 or a saltthereof.
 6. An ectoparasite controlling agent composition comprising (a)the benzyloxypyrimidine derivative according to claim 1 or a saltthereof as an active ingredient and (b) a domestic animal-acceptablecarrier.
 7. A method of controlling an ectoparasite, which comprisestreating the ectoparasite with an effective amount of thebenzyloxypyrimidine derivative according to claim 1 or a salt thereof.8. An agrohorticultural insecticide composition comprising (a) thebenzyloxypyrimidine derivative according to claim 2 or a salt thereof asan active ingredient and (b) an inert carrier.
 9. A method of using anagrohorticultural insecticide, which comprises treating a plant or soilwith the active ingredient of the agrohorticultural insecticideaccording to claim
 8. 10. A method of controlling an agrohorticulturalpest, which comprises treating a plant or soil with an effective amountof the benzyloxypyrimidine derivative according to claim 2 or a saltthereof.
 11. An ectoparasite controlling agent composition comprising(a) the benzyloxypyrimidine derivative according to claim 2 or a saltthereof as an active ingredient and (b) a domestic animal-acceptablecarrier.
 12. A method of controlling an ectoparasite, which comprisestreating the ectoparasite with an effective amount of thebenzyloxypyrimidine derivative according to claim 2 or a salt thereof.13. A composition comprising (a) the benzyloxypyrimidine derivativeaccording to claim 1 or a salt thereof and (b) an inert carrier.
 14. Acomposition comprising (a) the benzyloxypyrimidine derivative accordingto claim 2 or a salt thereof and (b) an inert carrier.